Ozone → HCID 66790401, compound

HRID 1510119Notes

Reaction equation

HRID 1510119 reaction equation
[O:1]=[O+][O-].[F:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C@H:12]([CH3:15])[CH2:13][CH3:14])=[CH:7][C:6]=1[CH:16]=C.[BH4-].[Na+]>ClCCl.CO>[F:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C@H:12]([CH3:15])[CH2:13][CH3:14])=[CH:7][C:6]=1[CH2:16][OH:1]

Participants

6

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 66791039HCID 66791039, compound

Product 1

HCID 66790401HCID 66790401, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ozone was bubbled through a −78° C. solution of 1-fluoro-4-{[(1R)-1-methylpropyl]oxy}-2-vinylbenzene (0.81 g, 4.17 mmol) in dichloromethane (27.8 ml) and MeOH (13.90 ml) until the reaction color remained blue. The reaction stirred 10 min, and then was purged with N2 for 10 min. MeOH (25 mL) was added, followed by sodium borohydride (0.237 g, 6.25 mmol). The reaction warmed to rt. After 1 h, the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on a silica gel cartridge (12% EtOAc/hexanes) to give the desired product.

Workup

  1. customwas purged with N2 for 10 min
  2. additionMeOH (25 mL) was added
  3. waitAfter 1 h
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customThe residue was purified by column chromatography on a silica gel cartridge (12% EtOAc/hexanes)

Sources & evidence

ORD record
ord-439a45ab375543998b0369bd7e457e59
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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