Vinyl Acetate → HCID 58158116, compound

HRID 1255506Notes

Reaction equation

HRID 1255506 reaction equation
[CH2:1]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[OH:11])[CH2:2][CH2:3][CH:4]=[CH2:5].[C:12](OC=C)(=[O:14])[CH3:13]>CCOCC>[C:12]([O:11][C@@H:7]1[CH2:8][CH2:9][CH2:10][C@H:6]1[CH2:1][CH2:2][CH2:3][CH:4]=[CH2:5])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 58158112HCID 58158112, compound

Product 1

HCID 58158116HCID 58158116, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

AMANO LIPASE PS (7.0 g, 64.7 mmol) was added to a solution of trans-2-pent-4-en-1-ylcyclopentanol (10.0 g, 64.7 mmol) and vinyl acetate (19.5 g, 129.4 mmol) in Et2O (275 mL). The mixture was stirred for 16 hours, then filtered through CELITE. The filtrate was concentrated to afford a residue that was purified by column chromatography on SiO2 (gradient elution, 0-100% Et2O/petroleum ether) to afford in the first fractions the title compound (5.43 g, 43%). 1H NMR (300 MHz, CDCl3) δ 5.89-5.72 (m, 1H), 5.00 (d, J=18.1 Hz, 1H), 495 (d, J=11.0 Hz, 1H), 4.82-4.73 (m, 1H), 2.11-1.98 (m, 2H), 2.03 (s, 3H), 1.98-1.85 (m, 3H), 1.71-1.60 (m, 3H), 1.50-1.35 (m, 3H), 1.29-1.14 (m, 2H); [α]D=−36.1 (c=0.73 in CHCl3). The later fractions contained enantio-enriched (1S,2S)-2-pent-4-en-1-ylcyclopentanol.

Workup

  1. filtrationfiltered through CELITE
  2. concentrationThe filtrate was concentrated
  3. customto afford a residue that
  4. customwas purified by column chromatography on SiO2 (gradient elution, 0-100% Et2O/petroleum ether)

Sources & evidence

ORD record
ord-6e85d9e5a214428dbeedf4447fa52af9
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

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