Cyclohexene → (+/-)-Ethyl 4-(4-hydroxyphenyl)-2-methyl-2-(methylsulfonyl)butanoate
Reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.C1CCCCC=1>[OH-].[OH-].[Pd+2].C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Pearlman's catalyst (Pd(OH)2/C, 1.19 g, 8.48 mmol) was added to a solution of (+/−)-Ethyl 4-[4-(benzyloxy)phenyl]-2-methyl-2-(methylsulfonyl)butanoate (4.73 g, 12.1 mmol) and cylcohexene (12.3 mL, 121 mmol) in ethanol (50 mL). The mixture was refluxed overnight. The reaction was filtered through celite (˜1 inch), washed with ethanol (100 mL) and ethyl acetate (200 mL), and the combined filtrates were concentrated in vacuo. The crude product was purified via column chromatography using an Analogiz SF15-40 g column and eluting with 500 mL 1:9 EtOAc:Heptane, and 1 L 1:1 EtOAc:Heptane to afford the title compound as a clear liquid (3.44 g, 94.6%) LC-MS m/z 301.1 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.33 (t, J=7.13 Hz, 3H) 1.70 (s, 3H) 2.10-2.24 (m, 1H) 2.37-2.53 (m, 2H) 2.62-2.78 (m, 1H) 3.04 (s, 3H) 4.26 (q, J=7.03 Hz, 2H) 5.77-6.01 (m, 1H) 6.77 (d, J=8.59 Hz, 2H) 7.01 (d, J=8.59 Hz, 2H).
Workup
- temperatureThe mixture was refluxed overnight
- filtrationThe reaction was filtered through celite (˜1 inch)
- washwashed with ethanol (100 mL) and ethyl acetate (200 mL)
- concentrationthe combined filtrates were concentrated in vacuo
- customThe crude product was purified via column chromatography
- washeluting with 500 mL 1:9 EtOAc
Sources & evidence
- ORD record
- ord-e9516d5f87674a008f378000e18db1ef
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853258B2
Reaction notes
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