HCID 18768147, compound → HCID 18768168, compound

HRID 480008Notes

Reaction equation

HRID 480008 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=4)[CH:17]=[CH:16][C:15]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:5]=[CH:4][C:3]1=2>[O-2].[Mn+2].ClCCl>[CH3:1][C:2]1([CH3:34])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]3[CH:19]=[C:18]([C:20]4[CH:21]=[CH:22][C:23]([CH:26]=[O:27])=[CH:24][CH:25]=4)[CH:17]=[CH:16][C:15]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 1

HCID 18768147HCID 18768147, compound

Product 1

HCID 18768168HCID 18768168, compound

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

640 mg (1.4 mmol) of the alcohol obtained in Example 51, 2.50 g (28.7 mmol) of manganese oxide and 50 ml of dichloromethane are mixed together in a 500 ml round-bottomed flask. The reaction medium is stirred for twenty hours at room temperature, the manganese oxide is then filtered off and the dichloromethane is evaporated off. The residue obtained is purified by chromatography on a column of silica eluted with a mixture composed of 80% heptane and 20% ethyl acetate. After evaporation of the solvents, 90 mg (14%) of the expected compound are collected in the form of a white powder with a melting point of 120-122° C.

Workup

  1. filtrationthe manganese oxide is then filtered off
  2. customthe dichloromethane is evaporated off
  3. customThe residue obtained
  4. customis purified by chromatography on a column of silica
  5. washeluted with a mixture
  6. customAfter evaporation of the solvents, 90 mg (14%) of the expected compound
  7. customare collected in the form of a white powder with a melting point of 120-122° C.

Sources & evidence

ORD record
ord-512768947f074977a6aba3e02f73db86
Source dataset
uspto-grants-2003_11
Patent number
US06649612B1

Reaction notes

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