Water → 3-Cyano-5-hydroxymethyl-thiophene-2-carboxylic acid methyl ester

HRID 1952648Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:12]Br)=[CH:8][C:9]=1[C:10]#[N:11])=[O:4].O.CC[O:17]C(C)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:12][OH:17])=[CH:8][C:9]=1[C:10]#[N:11])=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5-Bromomethyl-3-cyano-thiophene-2-carboxylic acid methyl ester (0.89 g, 3.42 mmol) and water (15 ml) in THF (2 ml) was heated at 70° C. for 2 d. The reaction mixture was cooled. The reaction mixture was poured into EtOAc (50 ml), washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by column (0-40% EtOAc in hexane) to give 0.1114 g (17%) yellow solid product.

Workup

temperatureThe reaction mixture was cooled
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe residue was purified by column (0-40% EtOAc in hexane)

Sources & evidence

ORD record: ord-d978820a730041b585e309c0eafbc154
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404859B2

Reaction notes

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