HCID 68510790, compound → HCID 59128269, compound

HRID 1715154Notes

Reaction equation

HRID 1715154 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH3:2]>ClCCl.O=[Mn]=O>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[CH3:2]

Participants

4

Reactant 1

HCID 68510790HCID 68510790, compound

Product 1

HCID 59128269HCID 59128269, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-ethoxy-4′-fluoro-biphenyl-4-yl)-methanol (0.43 g, 1.75 mmol, 1.0 equiv) in dichloromethane (20 mL) was added activated MnO2 (3.04 g, 34.92 mmol, 20.0 equiv) and the reaction mixture stirred vigorously for 3 h at ambient temperature. The reaction mixture was filtered over a pad of Celite, rinsed generously with dichloromethane and evaporated to dryness under reduced pressure. The crude material was purified with silica column chromatography eluting with hexane/ethyl acetate (4:1) to yield 0.33 g (77%) of the title compound as white crystals. MS (EI): 244.1 [M]+.

Workup

  1. filtrationThe reaction mixture was filtered over a pad of Celite
  2. washrinsed generously with dichloromethane
  3. customevaporated to dryness under reduced pressure
  4. customThe crude material was purified with silica column chromatography
  5. washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-c627d3c9be74487aa54593ace976f730
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

Loading…