Thiophenol → Methyl 3-(phenylsulfanyl)prop-2-enoate

HRID 2049836Notes

Reaction equation

HRID 2049836 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[C:7]1([SH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(N(CC)CC)C.CCOCC>[C:7]1([S:13][CH:3]=[CH:2][C:1]([O:5][CH3:6])=[O:4])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 7969ThiophenolHCID 13536Methyl propiolate

Product 1

HCID 54247095Methyl 3-(phenylsulfanyl)prop-2-enoate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2.45 g (24.54 mmol) methyl propiolate and 20 ml ether is treated with 2.7 g (24.54 mmol) benzenethiol with 4 drops triethylamine in 25 ml ether over 15 min at 20°. After stirring for 24 hr, the reaction mixture is rotoevaporated to yield methyl 3-phenylthio-2-propenoate.

Sources & evidence

ORD record
ord-8d34b6ab10a649caa33a48bc7b6d3b35
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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