Thioacetic acid, O-ethyl ester → (E)-ethyl-5-(3-methoxy-4-tert-butyldimethylsilyloxyphenyl)-3-oxopent-4-enothioate

HRID 476208Notes

Reaction equation

HRID 476208 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])/[CH:6]=[CH:7]/[C:8]([OH:10])=O.[C:22]([O:25][CH2:26][CH3:27])(=[S:24])[CH3:23]>C(OCC)(=O)C>[CH2:26]([O:25][C:22](=[S:24])[CH2:23][C:8](=[O:10])/[CH:7]=[CH:6]/[C:5]1[CH:11]=[CH:12][C:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:27]

Participants

4

Reactant 2

HCID 136711Thioacetic acid, O-ethyl esterHCID 11185931(2E)-3-{4-[(tert-butyldimethylsilyl)oxy]-3-methoxyphenyl}prop-2-enoic acid

Product 1

HCID 131731171(E)-ethyl-5-(3-methoxy-4-tert-butyldimethylsilyloxyphenyl)-3-oxopent-4-enothioateYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in the same manner as in Step 1 of Example C-1, except that an equimolar amount of each of trans-3-methoxy-4-tert-butyldimethylsilyloxy-cinnamic acid prepared in Step 1 of Example C-10 and ethyl thioacetate was used in place of trans-cinnamic acid and ethyl acetate.

Sources & evidence

ORD record
ord-523f6e87e5b340d98de8364de117ef24
Source dataset
uspto-grants-2014_01
Patent number
US08637674B2

Reaction notes

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