HCID 53787163, compound → HCID 54015276, compound

HRID 436528Notes

Reaction equation

HRID 436528 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][C:13]([CH:16]([O:19][CH3:20])[O:17][CH3:18])=[CH:14][CH:15]=1.[H][H]>[Ni].CO>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH:13]([CH:16]([O:17][CH3:18])[O:19][CH3:20])[O:12]1

Participants

5

Reactant 2

HCID 53787163HCID 53787163, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54015276HCID 54015276, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

8-(5-Dimethoxymethyl-2-furyl)-octanoic acid methyl ester (6.03 g, 0.02 mol), methanol (50 ml) and Raney nickel (3.0 g) were shaken under 100 atmospheres of hydrogen for 48 hours at 85°-100° C. After filtration, the methanol was distilled under reduced pressure from a water bath (60° C). Ether (50 ml) was added to the residue, and the turbid colourless solution was filtered. The ethereal solution was evaporated to dryness from a water bath under reduced pressure, at last under 15 mm Hg. The residual clear, colourless oil (6.07 g) was purified by distillation from a potassium acetate-coated flask giving 5.66 g (93%) of 8-(5-dimethoxymethyl-tetrahydro-2-furyl)-octanoic acid methyl ester, b0.1 126°-127° C, nD25 1.4504.

Workup

  1. filtrationAfter filtration
  2. distillationthe methanol was distilled under reduced pressure from a water bath (60° C)
  3. additionEther (50 ml) was added to the residue
  4. filtrationthe turbid colourless solution was filtered
  5. customThe ethereal solution was evaporated to dryness from a water bath under reduced pressure
  6. distillationThe residual clear, colourless oil (6.07 g) was purified by distillation from a potassium acetate-coated flask

Sources & evidence

ORD record
ord-88bc18d055f64eb7b5c4b6bb953339be
Source dataset
uspto-grants-1977_02
Patent number
US04009187

Reaction notes

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