3-(Hydroxymethyl)cyclohexanone → HCID 86703790, compound

HRID 1849912Notes

Reaction equation

HRID 1849912 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH2:4]1.[Cl:10][C:11]1[C:12](F)=[CH:13][C:14]([F:24])=[C:15]([CH:23]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].CC(C)([O-])C.[K+]>CS(C)=O.CCOC(C)=O>[Cl:10][C:11]1[C:12]([O:1][CH2:2][CH:3]2[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH2:4]2)=[CH:13][C:14]([F:24])=[C:15]([CH:23]=1)[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

Participants

6

Reactant 3

HCID 122016783-(Hydroxymethyl)cyclohexanoneHCID 23665647Potassium tert-butoxideHCID 58042499tert-butyl 5-chloro-2,4-difluorobenzoate

Product 1

HCID 86703790HCID 86703790, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(hydroxymethyl)cyclohexanone (575 mg) and tert-butyl 5-chloro-2,4-difluoro-benzoate (1.23 g) in DMSO (13.5 mL) at 14° C. (bath) was added potassium tert-butoxide (604 mg) gradually. After 5 min, the mixture was stirred at rt for 30 min. Diluted with EtOAc, the contents were washed with dilute NaHCO3 (3×) and brine, and dried (Na2SO4). After filtration and concentration, the crude was purified with flash chromatography (0->40% EtOAc/heptane) to give the product (445 mg).

Workup

  1. washthe contents were washed with dilute NaHCO3 (3×) and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationAfter filtration and concentration
  4. customthe crude was purified with flash chromatography (0->40% EtOAc/heptane)

Sources & evidence

ORD record
ord-df805d072b504918975dd95eccb0a289
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…