HCID 58929618, compound → HCID 58929678, compound

HRID 2360267Notes

Reaction equation

HRID 2360267 reaction equation
[F:1][C:2]1([F:10])[CH2:7][C@H:6]2[CH2:8][C@@H:3]1[CH2:4][C@@H:5]2[OH:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1([F:10])[CH2:7][C@H:6]2[CH2:8][C@@H:3]1[CH2:4][C:5]2=[O:9]

Participants

4

Reactant 2

HCID 58929618HCID 58929618, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 58929678HCID 58929678, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Silica gel 60 (particle size, 0.040-0.063 mm, CAS #63231-67-4, from EMD Chemical Inc. 4.0 g) was added to a solution of (1R,2S,4R)-5,5-difluorobicyclo[2.2.1]heptan-2-ol (0.800 g, 5.40 mmol) in anhydrous dichloromethane (20.0 ml). The mixture was cooled to 0° C., and pyridinium chlorochromate (1.86 g, 8.64 mmol) was added. The reaction mixture was warmed to ambient temperature and stirred at this temperature overnight. After this time, the mixture was diluted with dichloromethane (30 mL) and then filtered through a pad of silica gel. Removal of the solvents gave the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was warmed to ambient temperature
  2. filtrationfiltered through a pad of silica gel
  3. customRemoval of the solvents

Sources & evidence

ORD record
ord-0917861cf8cd45348e3042db2527822f
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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