HCID 53980569, compound → HCID 53745082, compound

HRID 2071664Notes

Reaction equation

HRID 2071664 reaction equation
[CH3:1][O:2][C:3](=[O:25])[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]=[CH:17][CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:12]1>[Ni].CO>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:12]1

Participants

4

Reactant 1

HCID 53980569HCID 53980569, compound

Product 1

HCID 53745082HCID 53745082, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

IV (1.77 g, 0.00500 mole), methanol (50 ml), and Raney nickel (1 g) were shaken under hydrogen at a pressure of 70 atmospheres for 24 hours at room temperature. After filtration, the solvent was removed from a water bath (60° C, 10 mm Hg). 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 (60° C, 10 mm Hg). The residual clear, colourless oil (1.90 g) was distilled under reduced pressure to give 1.69 g (95%) of VI as a colourless oil, b0.05 160°-172° C, nD25 1.4625.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed from a water bath (60° C, 10 mm Hg)
  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 (60° C, 10 mm Hg)
  6. distillationThe residual clear, colourless oil (1.90 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-e0fb7678eaff4a5da9e066ee3adf030f
Source dataset
uspto-grants-1977_09
Patent number
US04048198

Reaction notes

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