HCID 137329061, compound → HCID 178440052, compound

HRID 1681243Notes

Reaction equation

HRID 1681243 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([CH:16]([O:38][SiH:39]([CH3:41])[CH3:40])[C:17]1[C:18]([CH:35]([CH3:37])[CH3:36])=[N:19][C:20]([CH:32]([CH3:34])[CH3:33])=[C:21]([CH2:30][OH:31])[C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([CH:16]([O:38][SiH:39]([CH3:40])[CH3:41])[C:17]1[C:22]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)=[C:21]([CH:30]=[O:31])[C:20]([CH:32]([CH3:34])[CH3:33])=[N:19][C:18]=1[CH:35]([CH3:37])[CH3:36])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 137329061HCID 137329061, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 178440052HCID 178440052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.24 g (12.4 mmol) of neutral alumina and 2.7 g (12.4 mmol) of pyridinium chlorochromate are added to a solution of 2.7 g (6.2 mmol) of the compound from Example 6 in 50 ml of methylene chloride and the mixture is stirred for 1 h at room temperature. It is filtered over kieselguhr and washed with 200 ml of methylene chloride. The methylene chloride phase is concentrated in vacuo and the residue is chromatographed on a column (100 g of silica gel, 70-230 mesh, φ3.5 cm, using ethyl acetate/petroleum ether 1:9).

Workup

  1. filtrationIt is filtered over kieselguhr
  2. washwashed with 200 ml of methylene chloride
  3. concentrationThe methylene chloride phase is concentrated in vacuo
  4. customthe residue is chromatographed on a column (100 g of silica gel, 70-230 mesh, φ3.5 cm, using ethyl acetate/petroleum ether 1:9)

Sources & evidence

ORD record
ord-242ae6d6fd7e45629076686f8086a07c
Source dataset
uspto-grants-1992_12
Patent number
US05169857

Reaction notes

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