HCID 70818668, compound → HCID 70818711, compound

HRID 1850755Notes

Reaction equation

HRID 1850755 reaction equation
[CH:1]1([CH:4]([C:6]2[C:11]([F:12])=[CH:10][C:9]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:8][C:7]=2[F:23])[OH:5])[CH2:3][CH2:2]1.O([N+]1([O-])CCOCC1)C>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:1]1([C:4]([C:6]2[C:7]([F:23])=[CH:8][C:9]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)=[CH:10][C:11]=2[F:12])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 70818668HCID 70818668, compoundHCID 86711194HCID 86711194, compound

Product 1

HCID 70818711HCID 70818711, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclopropyl{2,6-difluoro-4-[(4-methoxybenzyl)oxy]phenyl}methanol (860 mg, 2.73 mmol) in DCM (137 mL) cooled to 0° C. via ice water bath was added 4-methoxylmorpholine N-oxide (481 mg, 4.10 mmol) followed by TPAP (96 mg, 0.27 mmol) and the resulting mixture was stirred for 20 minutes. The mixture was directly loaded onto a silica gel column (80 g, ISCO, eluting with a gradient of 10-30% ethyl acetate hexane) and purified to afford the title compound (728 mg, 85%). LC/MS 319 (M+H)+.

Workup

  1. washeluting with a gradient of 10-30% ethyl acetate hexane) and
  2. custompurified

Sources & evidence

ORD record
ord-b4228961841d4df482ac3201a6c9af1f
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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