HCID 10308881, compound → HCID 13773207, compound

HRID 236415Notes

Reaction equation

HRID 236415 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([C:15]1[CH:36]=[CH:35][CH:34]=[CH:33][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[C:25](=[O:32])[CH:26]=[C:27]([CH2:30][OH:31])[O:28][CH:29]=1)[CH2:13][CH3:14]>ClCCl.C(OCC)C>[O:32]=[C:25]1[C:24]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:16]2[CH:33]=[CH:34][CH:35]=[CH:36][C:15]=2[CH2:12][CH2:13][CH3:14])=[CH:29][O:28][C:27]([CH:30]=[O:31])=[CH:26]1

Participants

5

Reactant 2

HCID 10308881HCID 10308881, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13773207HCID 13773207, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4.44 g (20.6 mmole) of pyridinium chlorochromate in 50 ml of dichloromethane was added 3.46 g (10 mmole) of the title alcohol of Example 4 dissolved in 50 ml of dichloromethane. The resulting slurry was stirred at room temperature for twenty-four hours, then diluted with 100 ml of diethyl ether. The insolubles were removed by decanting and the supernatant was concentrated in vacuo. Purification by column chromatography afforded 1.4 g of the title compound, m.p. 95°-96°.

Workup

  1. customThe insolubles were removed
  2. customby decanting
  3. concentrationthe supernatant was concentrated in vacuo
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-4a1986c299e84204a857b165e9ed4239
Source dataset
uspto-grants-1987_02
Patent number
US04644071

Reaction notes

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