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Details for Patent: 4,380,635

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Details for Patent: 4,380,635

Title: Synthesis of acylated benzothiophenes
Abstract:A group of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-aminoethoxy)benzoyl]benzo[b]thiophen es are prepared by acylation of a methyl-protected starting compound followed by demethylation in a single reaction mixture.
Inventor(s): Peters; Mary K. (Indianapolis, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Filing Date:Dec 16, 1981
Application Number:06/331,046
Claims:1. A process for preparing a compound of the formula ##STR4## wherein R.sup.1 and R.sup.2 are independently C.sub.1 -C.sub.4 alkyl, or combine to form C.sub.4 -C.sub.6 polymethylene, --CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; which process comprises acylating a compound of the formula ##STR5## in the presence of aluminum chloride or aluminum bromide with an acylating agent of the formula ##STR6## wherein R.sup.4 is chloro or bromo; and adding to the reaction mixture a sulfur compound chosen from the group consisting of methionine and compounds of the formula

wherein X is hydrogen or unbranched C.sub.1 -C.sub.4 alkyl, and Y is C.sub.1 -C.sub.4 alkyl or phenyl.

2. A process of claim 1 wherein the product and the acylating agent are compounds wherein R.sup.1 and R.sup.2 combine to form tetramethylene.

3. A process of claim 1 wherein the product and the acylating agent are compounds wherein R.sup.1 and R.sup.2 combine to form pentamethylene.

4. A process of claim 1 wherein the product and the acylating agent are compounds wherein R.sup.1 and R.sup.2 combine to form --CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 --.

5. A process of any one of claims 1-4 wherein the catalyst is aluminum chloride.

6. A process of any one of claims 1-4 wherein the acylating agent is a compound wherein R.sup.4 is chloro.

7. A process of claim 5 wherein the acylating agent is a compound wherein R.sup.4 is chloro.

8. A process of any one of claims 1-4 wherein to the reaction mixture is added a C.sub.1 -C.sub.4 alkylthiol.

9. A process of claim 8 wherein the alkylthiol is ethanethiol.

10. A process of claim 5 wherein to the reaction mixture is added a C.sub.1 -C.sub.4 alkylthiol.

11. A process of claim 10 wherein the alkylthiol is ethanethiol.

12. A process of claim 7 wherein to the reaction mixture is added a C.sub.1 -C.sub.4 alkylthiol.

13. A process of claim 12 wherein the alkylthiol is ethanethiol.
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