HCID 53800149, compound → HCID 54427298, compound

HRID 1076028Notes

Reaction equation

HRID 1076028 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][C:13]([CH:16]=[CH:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:15]=1.[H][H]>[Ni].CO>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][C:13]([CH2:16][CH2:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 53800149HCID 53800149, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54427298HCID 54427298, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

III (11.37 g, 0.0326 mole), methanol (150 ml), and Raney nickel (2.5 g) were stirred at room temperature under 1 atmosphere of hydrogen, until one molequivalent of hydrogen had reacted. After filtration, the solvent was removed by distillation from a water bath (60°C) under reduced pressure, at last under 15 mm Hg. The residual, light yellow oil (11.4 g) was purified by preparative tlc (thin layer chromatography) on silica gel (mixture of petroleum ether (b.<50°C) and ether (2:1) as eluent). 7.25 g of the title compound were obtained as a yellowish oil. Further purification by distillation under nitrogen gave 7.05 g (62%) of the title compound as an almost colourless oil, b0.07 172°-180°C, nD25 1.4723.

Workup

  1. customhad reacted
  2. filtrationAfter filtration
  3. customthe solvent was removed by distillation from a water bath (60°C) under reduced pressure
  4. customThe residual, light yellow oil (11.4 g) was purified by preparative tlc (thin layer chromatography) on silica gel (mixture of petroleum ether (b.<50°C) and ether (2:1) as eluent)

Sources & evidence

ORD record
ord-01b39eef19034fa6ad2b430a65a9e2ed
Source dataset
uspto-grants-1976_05
Patent number
US03954813

Reaction notes

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