HCID 54555720, compound → HCID 53829428, compound

HRID 1076025Notes

Reaction equation

HRID 1076025 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[O:13][C:14]([CH:17]=[CH:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][CH:16]=1)[CH3:2].[H][H]>[Cu].C(O)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[O:13][C:14]([CH2:17][CH2:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][CH:16]=1)[CH3:2]

Participants

5

Reactant 2

HCID 54555720HCID 54555720, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53829428HCID 53829428, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent

Procedure

IV (1.74 g, 0.0048 mole), ethanol (25 ml), and Raney copper (Ponomarev et al., J.Gen.Chem. USSR 30 (1960) 584) (0.75 g) were shaken under 80 atmospheres of hydrogen for 6 hours at 30°C. After filtration, the ethanol was distilled under reduced pressure from a water bath (60°C). Ether (30 ml) was added to the residue, and the turbid solution was filtered (G4, Celite). The ethereal solution was evaporated to dryness from a water bath (50°C) under reduced pressure, at last under 15 mm Hg. The residual oil was purified by distillation under nitrogen. 1.51 g (86%) of V was hereby obtained as an almost colorless oil, b0.2 178°-181°C, nD25 1.4700.

Workup

  1. filtrationAfter filtration
  2. distillationthe ethanol was distilled under reduced pressure from a water bath (60°C)
  3. additionEther (30 ml) was added to the residue
  4. filtrationthe turbid solution was filtered (G4, Celite)
  5. customThe ethereal solution was evaporated to dryness from a water bath (50°C) under reduced pressure
  6. distillationThe residual oil was purified by distillation under nitrogen
  7. custom1.51 g (86%) of V was hereby obtained as an almost colorless oil, b0.2 178°-181°C

Sources & evidence

ORD record
ord-bd063cb86ca44d1f96b257af95ddbc60
Source dataset
uspto-grants-1976_05
Patent number
US03954813

Reaction notes

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