Methanol → 2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanone

HRID 271378Notes

Reaction equation

HRID 271378 reaction equation
C[OH:2].[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=C)[CH:13]([F:27])[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:2])[CH:13]([F:27])[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 69275764[1-({[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}methyl)vinyl]benzene

Product 1

HCID 692747802-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanoneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A methanol (300 mL) solution of [1-({[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}methyl)vinyl]benzene (2.02 g, 5.95 mmol) was cooled to −70° C. Ozone gas was bubbled through the solution until a blue color appeared. The solution was purged with nitrogen then a solution of triphenylphosphine (2.34 g, 8.92 mmol) in methylene chloride (100 mL) was added. Contents of the reaction flask were warmed to room temperature and the solvent was removed under reduced pressure. The remaining residue was subjected to flash column chromatography (hexane:ethyl acetate, 90:10) to give 2-{[4-(Benzyloxy)-2-fluorocyclohexyl]oxy}-1-phenylethanone as a colorless oil (1.68 g, 83% yield).

Workup

  1. customOzone gas was bubbled through the solution until a blue color
  2. customThe solution was purged with nitrogen
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-98a9f10ad5fe451da587fda9a348ffae
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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