Dimethylformamide → Methyl 2-(4-chlorophenyl)-2-cyclopentylacetate

HRID 1475635Notes

Reaction equation

CC(C)([O-])C.[K+].CN(C=O)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=1.[CH:24]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25]1>O>[CH3:23][O:22][C:20](=[O:21])[CH:19]([C:16]1[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=1)[CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 3.65 g (32.5 mmol) of potassium tert-butoxide in 65 ml of abs. DMF was cooled to 0° C., and a solution of 5.0 g (27.08 mmol) of methyl 4-chlorophenylacetate in about 2 ml of abs. DMF was added dropwise. The mixture was stirred at 0° C. for 30 min, and 4.84 g (32.5 mmol) of cyclopentyl bromide were then slowly added dropwise. The reaction mixture was stirred at 0° C. for 1 h and then added to water and extracted with ethyl acetate. The organic phase was dried over sodium sulphate and concentrated under reduced pressure, and the residue was dried under high vacuum. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 100:1). This gave 6.28 g of the target compound (91.8% of theory).

Workup

stirringThe reaction mixture was stirred at 0° C. for 1 h
extractionextracted with ethyl acetate
dry with materialThe organic phase was dried over sodium sulphate
concentrationconcentrated under reduced pressure
customthe residue was dried under high vacuum
customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 100:1)

Sources & evidence

ORD record: ord-4a08885d9f9b4b2d941e60a0b4f19a74
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018258B2

Reaction notes

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