HCID 10698227, compound → HCID 10840687, compound

HRID 2294901Notes

Reaction equation

HRID 2294901 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]4[CH:43]=[CH:42][C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[N:35]=4)=[CH:28][CH:27]=3)[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]4[CH:43]=[CH:42][C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[N:35]=4)=[CH:28][CH:27]=3)[CH2:20][CH2:21][C:22](=[O:25])[CH2:23][CH2:24]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 10698227HCID 10698227, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 10840687HCID 10840687, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

To a mixture of 4,4-bis(4-(2-quinolylmethoxy)phenyl)cyclohexanol (resulting from Example 4) (1.13 g, 2 mmol) and molecular sieves (3 g) in CH2 Cl2 (40 mL) was added PCC (0.65 g, 3 mmol) and the resulting mixture was stirred at room temperature for 30 min. The mixture was filtered through the Celite, the filtrate was concentrated in vacuo to 10 mL and then chromatographed (silica gel, 4:1 CH2Cl2 /EtOAc) to afford 0.25 g of 4,4-bis(4-(2-quinolylmethoxy) phenyl)cyclohexanone.

Workup

  1. filtrationThe mixture was filtered through the Celite
  2. concentrationthe filtrate was concentrated in vacuo to 10 mL
  3. customchromatographed (silica gel, 4:1 CH2Cl2 /EtOAc)

Sources & evidence

ORD record
ord-48005c1754764386aad8c24e119df57d
Source dataset
uspto-grants-1997_11
Patent number
US05691351

Reaction notes

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