Triethylamine → 2-(4-Fluorophenyl)cyclohexan-1-one

HRID 347299Notes

Reaction equation

HRID 347299 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[OH:14])=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 20487437HCID 20487437, compound

Product 1

HCID 130895402-(4-Fluorophenyl)cyclohexan-1-oneYield 95%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

bii) Alternatively, to a solution of rac-2-(4-fluoro-phenyl)-cyclohexanol (7.5 g, 39 mmol) in dry DMSO (67 mL) was added triethylamine (27 mL, 190 mmol) under argon and the resulting mixture cooled to 0° C. and then a solution of sulfur trioxide pyridine complex (18.4 g, 116 mmol) in dry DMSO (98 mL) was added dropwise over 15 min. After 1 h, the mixture was diluted with water (200 mL) and the product extracted with DCM (2×100 mL). The combined organic extracts were then dried over sodium sulfate, followed by filtration and evaporation. Purification by filtration through silica gel, eluting with ethyl acetate:hexane (1:4) afforded the title compound (7.1 g, 95%) as white crystals. MS: m/e=192.1 (M).

Workup

  1. extractionthe product extracted with DCM (2×100 mL)
  2. dry with materialThe combined organic extracts were then dried over sodium sulfate
  3. filtrationfollowed by filtration and evaporation
  4. customPurification
  5. filtrationby filtration through silica gel
  6. washeluting with ethyl acetate:hexane (1:4)

Sources & evidence

ORD record
ord-d5e61e2b2f6f428c8588fbf10a361152
Source dataset
uspto-grants-2007_02
Patent number
US07173133B2

Reaction notes

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