Acetaldehyde → HCID 86608956, compound

HRID 505330Notes

Reaction equation

CCCCCC.[C:7]([O:11][C:12](=[O:22])[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1Br)([CH3:10])([CH3:9])[CH3:8].[CH:23](=[O:25])[CH3:24].[Cl-].[NH4+]>C1COCC1.O>[C:7]([O:11][C:12](=[O:22])[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[CH:23]([OH:25])[CH3:24])([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: -78 °C

Procedure

At −78° C. under nitrogen 1.6 M butyllithium solution in hexane (4.89 ml, 7.8 mmol) were added dropwise to [2-bromo-4-chloro-phenyl]-carbamic acid tert-butyl ester (1.09 g, 3.56 mmol) in THF (20 ml). The reaction was stirred for 15 minutes at −78° C. and acetaldehyde (235 mg, 5.33 mmol) was added dropwise. After stirring for 15 minutes at −78° C. saturated aqueous ammonium chloride solution was added and the reaction was allowed to warm to room temperature. The reaction was diluted with water and extracted twice with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated to yield the crude product which was purified by column chromatography (heptane:ethyl acetate=4:1). The product was isolated as a colorless viscous oil (525 mg, 54%).

Workup

additionwas added
temperatureto warm to room temperature
extractionextracted twice with diethyl ether
washThe combined organic layers were washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent was evaporated
customto yield the crude product which
customwas purified by column chromatography (heptane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-fcf4a0d7a3f34850a58013d3492fa523
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781441B2

Reaction notes

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