Ethyl Thioglycolate → HCID 59497930, compound

HRID 1676113Notes

Reaction equation

Cl[CH:2]=[C:3]([CH2:9][CH2:10][CH3:11])[C:4](=O)[CH:5]([CH3:7])[CH3:6].C([O:14][C:15](=[O:18])[CH2:16][SH:17])C>>[CH:5]([C:4]1[C:3]([CH2:9][CH2:10][CH3:11])=[CH:2][S:17][C:16]=1[C:15]([OH:18])=[O:14])([CH3:7])[CH3:6]

Participants

Reactant 2

HCID 12185Ethyl Thioglycolate

HCID 86645769HCID 86645769, compound

Product 1

HCID 59497930HCID 59497930, compoundYield 30.5%

Procedure

1-Chloro-4-methyl-2-propyl-pent-1-en-3-one (29.7 g, 170 mmol) is reacted with mercaptoacetic acid ethyl ester (40.9 g, 340 mmol) in analogy to the procedure given for Intermediate A7 to give 3-isopropyl-4-propyl-thiophene-2-carboxylic acid (11.0 g) as colourless crystals; 1H NMR (CD3OD): δ 7.21 (s, 1H), 3.83 (hept, J=7.0 Hz, 1H), 2.60 (t, J=7.6 Hz, 2H), 1.70-1.56 (m, 2H), 1.33 (d, J=7.6 Hz, 6H), 0.99 (t, J=7.6 Hz, 3H).

Sources & evidence

ORD record: ord-4572d4e2565c45c2844b0237c9040ae5
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003800B2

Reaction notes

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