Triethylamine → p-Toluenesulfonic acid

HRID 363721Notes

Reaction equation

HRID 363721 reaction equation
S1C2C(CNCC2)=CC1=O.[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([Si](C)(C)Cl)(C)(C)C.C(N(CC)CC)C.[Si](OC1SC2CCNCC=2C=1)(C(C)(C)C)(C)C>C(Cl)Cl>[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 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 15392095HCID 15392095, compoundHCID 451083204-Methylbenzene-1-sulfonic acid--5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one (1/1)

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

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-butyl-dimethylchlorosilane, 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, 2.40 g of 2-chlorobenzyl chloride and 3.02 g of triethylamine were added thereto, and the mixture was allowed to react under stirring at 40° C. for 8 hours.

Sources & evidence

ORD record
ord-7dad5dac702e483eb0de331a78fc79f7
Source dataset
uspto-grants-1999_02
Patent number
US05874581

Reaction notes

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