HCID 54139094, compound → HCID 22560983, compound

HRID 2249037Notes

Reaction equation

HRID 2249037 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH2:22][OH:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=1)[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH:22]=[O:23])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 54139094HCID 54139094, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 22560983HCID 22560983, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

10 g (30 mmol) of 7-(4-ethoxycarbonylphenyl)-6-hydroxymethylheptanoic acid ethyl ester are dissolved in 100 ml of methylene chloride of analytical purity and methylene chloride containing 6.45 g (30 mmol) of pyridinium chlorochromate is added under cooling with tapwater. After stirring for 2 hours at room temperature 3.25 g (15 mmol) of pyridinium chlorochromate are once again added and the mixture is stirred for 1 hour. The reaction mixture (including the oily residue) is applied to a chromatographic column filled with 500 g of silica gel (Merck Si 60, 0.04-0.063 mm) and elution is carried out under a slightly elevated pressure using methylene chloride as the mobile solvent. A fraction is thus obtained which, after being evaporated in vacuo, yields 7.7 g of an oily product.

Workup

  1. additionis added
  2. temperatureunder cooling with tapwater
  3. additionare once again added
  4. additionfilled with 500 g of silica gel (Merck Si 60, 0.04-0.063 mm) and elution
  5. customA fraction is thus obtained which
  6. customafter being evaporated in vacuo

Sources & evidence

ORD record
ord-13dd94fd82ff4e2d99c4901ebad487f1
Source dataset
uspto-grants-1991_08
Patent number
US05041638

Reaction notes

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