p-Toluenesulfonic acid → HCID 86753744, compound

HRID 363722Notes

Reaction equation

HRID 363722 reaction equation
[S:1]1[CH:9]2[C:4]([CH2:5][NH:6][CH2:7][CH2:8]2)=[CH:3][C:2]1=[O:10].[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:16][CH:17]=1.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>C(Cl)Cl>[Si:26]([O:10][C:2]1[S:1][C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 137484635,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one

Product 1

HCID 86753744HCID 86753744, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.00 g of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one.p-toluenesulfonate, 2.47 g of tert-butyldimethylchlorosilane, 1.66 g of triethylamine and 15 ml of methylene chloride was stirred at room temperature (20° C.) for 3 hours. The produced 2-(tert-butyldimethylsilyloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-p-toluenesulfonate was not isolated, 5.90 g of 2-chloro-α-methoxycarbonylbenzyl bromide and 3.02 g of triethylamine were added thereto, and the mixture was allowed to react.

Sources & evidence

ORD record
ord-e7f1f02c142945aeacad3ea3cf4f5251
Source dataset
uspto-grants-1999_02
Patent number
US05874581

Reaction notes

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