Hydrochloric Acid → 1-Cyclopentyl-pent-4-yn-1-one

HRID 858868

Reaction equation

N1C=CC=CC=1S[C:8](=[O:13])[CH2:9][CH2:10][C:11]#[CH:12].[CH:14]1([Mg]Br)[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>C1COCC1>[CH:14]1([C:8](=[O:13])[CH2:9][CH2:10][C:11]#[CH:12])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of pent-4-ynethioic acid S-pyridin-2-yl ester (17.9 g, 94 mmol), dissolved in THF (900 mL) cooled to −78° C. was added cyclopentylmagnesium bromide (2.0 M, 94 mL, 188.5 mmol). The reaction was stirred for 15 minutes, and then warmed to −50° C. The reaction was poured into 500 mL 1 N HCl and the layers were separated. The aqueous layer was extracted with 2×200 mL diethyl ether and the organic layers were combined. The organics were then washed with 300 mL of 1 N NaOH. The organic layer was dried over Mg SO4, and the solids were removed by filtration. The solvent was removed by rotary evaporation to give the desired compound (14.0 g, 99% yield).

Workup

temperaturewarmed to −50° C
customthe layers were separated
extractionThe aqueous layer was extracted with 2×200 mL diethyl ether
washThe organics were then washed with 300 mL of 1 N NaOH
dry with materialThe organic layer was dried over Mg SO4
customthe solids were removed by filtration
customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record: ord-f920eae2f20c4242a34a21514f08dce6
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Linked notes

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