Acetyl chloride → 2-Phenylbicyclo[1.1.1]pentan-2-yl acetate

HRID 2280802Notes

Reaction equation

[C:1]1([C:7]2([OH:12])[CH:10]3[CH2:11][CH:8]2[CH2:9]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](Cl)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:12][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]2[CH2:9][CH:10]1[CH2:11]2)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 2.7 g (16.8 mmol) of 2-phenylbicyclo[1.1.1]pentan-2-ol in pyridine (15 mL) at 0° C. was added dropwise acetyl chloride (1.5 mL, 21.0 mmol) in a nitrogen atmosphere. The reaction mixture was stirred for 0.5 h at 0° C. and for 1 h at room temperature. The solution was poured onto ice and extracted with 50 mL of diethyl ether twice. The combined diethyl ether solution was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous copper sulfate solution. After drying over anhydrous magnesium sulfate, the solution was concentrated and the crude product was purified by column chromatography (0-5% ethyl acetate in petroleum ether) to give the desired product (2.7 g, 13.4 mmol, yield: 80%). 1H NMR (400 MHz, CDCl3) δ ppm 7.47-7.26 (m, 5H), 3.31 (s, 2H), 2.43 (dd, J1=10.4 Hz, J2=2.8 Hz, 1H), 1.95 (s, 3H), 1.80 (d, J=2.8 Hz, 1H), 1.66 (d, J=3.2 Hz, 1H), 1.49 (dd, J1=10.4, J2=3.2 Hz, 1H).

Workup

additionThe solution was poured onto ice
extractionextracted with 50 mL of diethyl ether twice
washThe combined diethyl ether solution was washed with saturated aqueous sodium bicarbonate solution and with saturated aqueous copper sulfate solution
dry with materialAfter drying over anhydrous magnesium sulfate
concentrationthe solution was concentrated
customthe crude product was purified by column chromatography (0-5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-be48bf92027c4b07bd4ffad501436aa3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139534B2

Reaction notes

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