Acetyl chloride → HCID 86628106, compound

HRID 2245241Notes

Reaction equation

HRID 2245241 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][OH:23])[C@@H:18]([CH2:24][OH:25])[C@@H:17]2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:35](Cl)(=[O:37])[CH3:36]>ClCCl>[C:35]([O:23][CH2:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([O:15][C@@H:13]([C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=2)[CH3:14])[C@@H:17]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[C@@H:18]1[CH2:24][OH:25])(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 42639484((1S,2R,3R,4S)-4-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)cyclohexane-1,2-diyl)dimethanol

Product 1

HCID 86628106HCID 86628106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(1S,2R,3R,4S)-4-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)cyclohexane-1,2-diyl]dimethanol (3.3 g, 6.7 mmol, intermediate step J) in dichloromethane (50 mL) were added acetyl chloride (0.52 mL, 7.4 mmol) and TEA (1.1 mL, 7.9 mmol) at room temperature. The resulting mixture was stirred at r.t. for 6 hr. The solvent was removed under vacuum and the residue was separated by column chromatography on silica gel eluting with 3:1 hexane:ethyl acetate. The less polar mono-alcohol on TLC was collected (0.75 g). MS: (MH)+ 536.2.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was separated by column chromatography on silica gel eluting with 3:1 hexane
  3. customThe less polar mono-alcohol on TLC was collected (0.75 g)

Sources & evidence

ORD record
ord-7edae7f49cbe4d6faeeee2732db9ac28
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

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