HCID 54220868, compound → HCID 13829867, compound

HRID 1731561Notes

Reaction equation

HRID 1731561 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[CH:4]1[CH2:10][CH2:11][CH2:12][CH:13]=[CH:14][C:15]([O:17][CH3:18])=[O:16]>CO.[Pd]>[OH:1][CH2:2][CH:3]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[CH:4]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 1

HCID 54220868HCID 54220868, compound

Product 1

HCID 13829867HCID 13829867, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

28.7 g (0.11 mole) of methyl 6-(3-hydroxymethylbicyclo[2.2.1]hept-2-yl)-hex-2-enoate are hydrogenated in 450 ml of methanol, with the addition of 12 g of palladium-on-charcoal (5% strength), at 60° C. under a pressure of 30 bar for 11/2 hours. The catalyst is removed by filtration, the methanol is evaporated off in vacuo and the oil which remains is chromatographed on silica gel, using methylene chloride/methanol (99:1), to give 25.5 g (91% yield) of methyl 6-(3-hydroxymethyl-bicyclo[2.2.1]hept-2-yl)-hexanoate.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe methanol is evaporated off in vacuo
  3. customthe oil which remains is chromatographed on silica gel

Sources & evidence

ORD record
ord-431a2b8df721424d93b4a341e307322d
Source dataset
uspto-grants-1986_11
Patent number
US04622339

Reaction notes

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