Water → Racemic 2-allylcyclopropyl acetate
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[CH2:1]([CH:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[OH:9])C=C.C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18].O>CC1OCCC1>[C:17]([O:9][CH:5]1[CH2:6][CH:7]1[CH2:8][CH:4]=[CH2:1])(=[O:19])[CH3:18][CH2:1]([CH:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[OH:9])C=C.C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18].O>CC1OCCC1>[C:17]([O:9][CH:5]1[CH2:6][CH:7]1[CH2:8][CH:4]=[CH2:1])(=[O:19])[CH3:18]Into a reaction vessel was added 2-allylcyclopentanol M (1 equivalent) in MeTHF (10 volumes). The vessel was purged with nitrogen and the solution was then cooled to 0° C. Triethylamine (3.0 equivalents) was then slowly added to the solution over about 30 minutes. The mixture was allowed to stir for about 30 minutes after which acetyl chloride (2.5 equivalents) was added maintaining the internal temperature about below 20° C. The reaction was then allowed to stir for at least 12 hours at about 21° C. After the allotted time, water (6 volumes) was slowly charged to the reactor and the phases were separated. The organic layer was then washed with 2M hydrochloric acid (6 volumes), 10 wt. % sodium bicarbonate (6 volumes) and then brine (6 volumes). The organic layer is concentrated under reduced pressure at about 0° C. to obtain crude racemic 2-allylcyclopropyl acetate N. 1H NMR (400 MHz, CDCl3): δ 5.85-5.73 (m, 1H), 5.10-5.04 (m, 1H), 5.00-4.97 (m, 1H), 3.85-3.82 (m, 1H), 2.13-2.07 (m, 1H), 1.99 (s, 3H), 2.01-1.89 (m, 1H), 1.14-1.03 (m, 1H), 0.87-0.76 (m, 1H), 0.64-0.57 (m, 1H).
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