Dimethyl Sulfoxide → [1-(2-Oxo-ethyl)-cyclohexyl]-acetic acid benzyl ester

HRID 455901Notes

Reaction equation

HRID 455901 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[CH2:10][C:11]1([CH2:17][CH2:18][OH:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.C(N(CC)C(C)C)(C)C>ClCCl>[CH2:1]([O:8][C:9](=[O:20])[CH2:10][C:11]1([CH2:17][CH:18]=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 66675168[1-(2-Hydroxy-ethyl)-cyclohexyl]-acetic acid benzyl ester

Product 1

HCID 86631099[1-(2-Oxo-ethyl)-cyclohexyl]-acetic acid benzyl esterYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of [1-(2-hydroxy-ethyl)-cyclohexyl]-acetic acid benzyl ester (1.3 g, 47 mmol), dimethyl sulfoxide (0.83 mL, 12 mmol), and N,N-diisopropylethylamine (2.0 mL, 12 mmol) in dichloromethane (20 mL) was cooled to 0° C. and sulfur trioxide-pyridine complex (1.9 g, 12 mmol) was added. The reaction mixture was stirred at 0° C. for 2 h and the reaction was quenched with 0.1 N HCl. The aqueous layer was discarded. The organic extract was washed twice with 0.1 N HCl and brine. The organic extract was dried with sodium sulfate, filtered, and concentrated to dryness to provide the title compound (1.17 g).

Workup

  1. additionsulfur trioxide-pyridine complex (1.9 g, 12 mmol) was added
  2. customthe reaction was quenched with 0.1 N HCl
  3. extractionThe organic extract
  4. washwas washed twice with 0.1 N HCl and brine
  5. extractionThe organic extract
  6. dry with materialwas dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-48035ff6ea504c1888589d2cabb1502e
Source dataset
uspto-grants-2013_07
Patent number
US08497287B2

Reaction notes

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