Dichloromethane → 1-[3~4~-(Trifluoromethoxy)[1~1~,1~2~,1~3~,1~4~,1~5~,1~6~-hexahydro[1~1~,2~1~:2~4~,3~1~-terphenyl]]-1~4~-yl]pentan-2-one

HRID 1856588Notes

Reaction equation

HRID 1856588 reaction equation
[OH:1][CH:2]([CH2:27][CH2:28][CH3:29])[CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C(Cl)Cl>C1(C)C=CC=CC=1>[O:1]=[C:2]([CH2:27][CH2:28][CH3:29])[CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 22131650HCID 22131650, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 221317411-[3~4~-(Trifluoromethoxy)[1~1~,1~2~,1~3~,1~4~,1~5~,1~6~-hexahydro[1~1~,2~1~:2~4~,3~1~-terphenyl]]-1~4~-yl]pentan-2-oneYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4'-(4-(2-Hydroxypentyl)cyclohexyl)-4-trifluoromethoxybiphenyl (12.3 mmol) was added at 0 or below in the absence of a solvent to a mixture of PCC (13.5 mmol), 3 g of silica gel, and 70 ml of methylene chloride, and the mixture was stirred at room temperature for 7 hr to give a black suspension. 500 ml of toluene was added thereto, and the mixture was stirred. The precipitated insolubles were filtered off through Celite, and the solvent was distilled off from the resultant black solution under reduced pressure to give a dark brown crude product. The crude product was purified by silica gel column chromatography (eluting solution: toluene) to give 4'-(4-(2-oxopentyl)cyclohexyl)-4-trifluoromethoxybiphenyl (7.4 mmol, yield 66%) as a white crystal.

Workup

  1. customto give a black suspension
  2. stirringthe mixture was stirred
  3. filtrationThe precipitated insolubles were filtered off through Celite
  4. distillationthe solvent was distilled off from the resultant black solution under reduced pressure
  5. customto give a dark brown crude product
  6. customThe crude product was purified by silica gel column chromatography (eluting solution: toluene)

Sources & evidence

ORD record
ord-b8f566e01a3b4606bbb05007c3b7de6d
Source dataset
uspto-grants-2000_11
Patent number
US06143198

Reaction notes

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