Water → HCID 54558366, compound

HRID 1731559Notes

Reaction equation

HRID 1731559 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[CH:4]1[CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:20].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C)C=O>[C:2]([CH:3]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[CH:4]1[CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])([OH:20])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 53957852HCID 53957852, compound

Product 1

HCID 54558366HCID 54558366, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 25.0 g (0.1 mole) of methyl 6-(3-hydroxymethyl-bicyclo[2.2.1]hept-2-yl)-hex-5-enoate in 60 ml of absolute dimethylformamide is added to 132.0 g (0.35 mole) of pyridinium dichromate in 200 ml of absolute dimethylformamide at 20° C. The reaction mixture is stirred at 20° C. for 9 hours, left to stand for 14 hours and then poured into 1.9 liters of water and extracted with diethyl ether. After drying over Na2SO4, the mixture is evaporated in vacuo and the residue is chromatographed on silica gel, using methylene chloride/methanol (95:5) to give 17.3 g of methyl 6-(3-carboxy-bicyclo-[2.2.1]hept-2-yl)-hex-5-enoate (yield: 65%)

Workup

  1. waitleft
  2. waitto stand for 14 hours
  3. extractionextracted with diethyl ether
  4. dry with materialAfter drying over Na2SO4
  5. customthe mixture is evaporated in vacuo
  6. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-b7cd5d73557f4eab969a427a5a9cc05c
Source dataset
uspto-grants-1986_11
Patent number
US04622339

Reaction notes

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