Hydrochloric Acid → 5-Ethynylthiophene-2-carboxylic acid
Reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([O:12]CC)=[O:11])=[CH:7][CH:6]=1.[Li+].[OH-].O.Cl>C1COCC1>[C:4]([C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1)#[CH:3]Participants
6
Conditions
- Temperature
- 40 °C
Procedure
To a solution of ethyl 5-(2-trimethylsilyl-ethyn-1-yl)-thiophene-2-carboxylate prepared above (529 mg, 2.10 mmol) in THF (20 mL), 1N aq. LiOH (7.0 mL, 7.0 mmol) was added. After the mixture was stirred at 40° C. overnight, it was poured into water. The aqueous solution was acidified with 1N HCl to pH 1. The product was extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, concentrated in vacuo to give 5-ethynyl-thiophene-2-carboxylic acid (316 mg). MS 153 (M+H).
Workup
- extractionThe product was extracted with EtOAc
- washThe EtOAc solution was washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c905c3574124465c9e85da3f6fc0ab1b
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767697B2
Reaction notes
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