HCID 58592523, compound → HCID 58592526, compound

HRID 1178846Notes

Reaction equation

HRID 1178846 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][O:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][O:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]1

Participants

4

Reactant 2

HCID 58592523HCID 58592523, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 58592526HCID 58592526, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclopentanol (142 mg) in dichloromethane (10 mL) at room temperature were added pyridinium chlorochromate (146 mg) and powdered 4 A° molecular sieves (146 mg), and the resulting mixture was stirred at room temperature for 1.5 h and then filtered through a small pad of silica gel. The filtrate was evaporated in vacuo and the residue was purified by preparative TLC eluting with 30% ethyl acetate/70% hexanes to give the title compound as an oily material (150 mg). 1H NMR (400 MHz, CDCl3) δ 2.3-2.6 (4H, m), 2.68 (1H, d, J=17.6 Hz), 2.76 (1H, d, J=17.6 Hz), 3.52 (1H, q, J=9.2 Hz), 3.58 (1H, d, J=9.2 Hz), 4.52 (2H, s), 7.2-7.4 (5H, m), 7.59 (2H, s), 7.76 (1H, s).

Workup

  1. filtrationfiltered through a small pad of silica gel
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by preparative TLC
  4. washeluting with 30% ethyl acetate/70% hexanes

Sources & evidence

ORD record
ord-6e343476be5f4085ab36b123aa969607
Source dataset
uspto-grants-2007_10
Patent number
US07276631B2

Reaction notes

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