Acetaldehyde → HCID 67314423, compound

A solution of thiophene-2-carboxylic acid ethylamide (465 mg, 3 mmol) in dry THF (12 mL) is cooled to −78° C. under an argon atmosphere. Tert-BuLi (5.3 mL of a 1.7 M solution in pentane, 9.0 mmol) is added dropwise at −78° C. and the reaction mixture is stirred for 3 h. The reaction mixture is treated with neat acetaldehyde (3 mL, 53 mmol) and is stirred at −78° C. for 2 h and then warmed to room temperature overnight. The reaction mixture is quenched by the addition of water (35 mL). The reaction mixture is transferred to a separatory funnel and the organic phase is collected. The aqueous layer is extracted 5 times with Dichloromethane. The combined organic extracts are washed with water, and saturated aqueous NaCl, dried over Na2SO4 and concentrated. The residue is purified by chromatography (silica gel, 25% EtOAc/hexane) to give the title compound (298 mg, 15 mmol) in 50% yield.

1. stirringis stirred at −78° C. for 2 h
2. customThe reaction mixture is quenched by the addition of water (35 mL)
3. customThe reaction mixture is transferred to a separatory funnel
4. customthe organic phase is collected
5. extractionThe aqueous layer is extracted 5 times with Dichloromethane
6. washThe combined organic extracts are washed with water, and saturated aqueous NaCl
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customThe residue is purified by chromatography (silica gel, 25% EtOAc/hexane)

ORD record

ord-59963f63b29a45b69e72139206bc3e64

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455535B2