HCID 178505693, compound → HCID 178520600, compound

HRID 726493Notes

Reaction equation

HRID 726493 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=2[F:29])[CH2:18][CH2:17]1)C1C=CC=CC=1>C(O)C>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]1[CH2:17][CH2:18][C@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=2[F:29])[CH2:20][CH2:21]1

Participants

3

Reactant 1

HCID 178505693HCID 178505693, compound

Product 1

HCID 178520600HCID 178520600, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 6.5 g of 1-[trans-4-(7-benzyloxy-1-heptenyl)cyclohexyl]-2,3-difluorobenzene, 1 g of 10% Pd--C, and 50 ml of ethanol were placed in a 300 ml autoclave. The mixture was stirred at room temperature for 2 days under a hydrogen pressure of 10 kg/cm2. A catalyst was filtered away and a filtrate was concentrated. Thereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=3/1) and recrystallized from hexane to obtain 3.5 g of 1-[trans-4-(7-hydroxyheptyl)cyclohexyl]-2,3-difluorobenzene (Y: 69.6%). The compound thus obtained had a purity of 98.5% by GC.

Workup

  1. filtrationA catalyst was filtered away
  2. concentrationa filtrate was concentrated
  3. customThereafter, the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=3/1)
  4. customrecrystallized from hexane

Sources & evidence

ORD record
ord-bbbd1982c6e544dd96ad455aa13e3c4f
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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