Ethanol → HCID 21685070, compound

HRID 1029984Notes

Reaction equation

HRID 1029984 reaction equation
[C:1](=[O:55])([O:24][C:25]1[C:26]([CH3:54])=[C:27]2[C:32](=[C:33]([CH3:36])[C:34]=1[CH3:35])[O:31][C:30]([CH3:53])([CH2:37][CH2:38][CH2:39][CH:40]([CH3:52])[CH2:41][CH2:42][CH2:43][CH:44]([CH3:51])[CH2:45][CH2:46][CH2:47][CH:48]([CH3:50])[CH3:49])[CH2:29][CH2:28]2)[O:2][CH:3]([CH2:15][O:16]CC1C=CC=CC=1)[CH:4]([OH:14])[CH2:5][O:6]CC1C=CC=CC=1.C(O)C.[H][H]>[C].[Pd].C(O)(=O)C>[C:1](=[O:55])([O:24][C:25]1[C:26]([CH3:54])=[C:27]2[C:32](=[C:33]([CH3:36])[C:34]=1[CH3:35])[O:31][C:30]([CH3:53])([CH2:37][CH2:38][CH2:39][CH:40]([CH3:52])[CH2:41][CH2:42][CH2:43][CH:44]([CH3:51])[CH2:45][CH2:46][CH2:47][CH:48]([CH3:49])[CH3:50])[CH2:29][CH2:28]2)[O:2][CH:3]([CH2:15][OH:16])[CH:4]([OH:14])[CH2:5][OH:6]

Participants

6

Reactant 3

HCID 702EthanolHCID 21685083HCID 21685083, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21685070HCID 21685070, compoundYield 128.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture comprising 4.4 g of 3-benzyloxy-1-benzyloxymethyl-2-hydroxypropyl 2,5,7,8-tetramethyl-2-(4',8', 12'-trimethyltridecyl)-6-chromanyl carbonate, 0.5 g of 5% palladium carbon, 150 ml of ethanol and 5 ml of acetic acid was catalytically reduced in a hydrogen gas stream of 4 kg/cm2 until no hydrogen was absorbed any more (approximately 6 hours). After filtering off the catalyst, the filtrate was concentrated to thereby reduce the amount to approximately 1/3. Then it was poured into water and extracted with ether. The extract was successively washed with an aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate. After distilling off the solvent, the obtained oily residue was purified by column chromatography (silica gel, hexane : ethyl acetate=2:1) to thereby give 4.3 g of the title compound as a colorless viscous liquid.

Workup

  1. customwas absorbed any more (approximately 6 hours)
  2. filtrationAfter filtering off the catalyst
  3. concentrationthe filtrate was concentrated
  4. additionThen it was poured into water
  5. extractionextracted with ether
  6. washThe extract was successively washed with an aqueous solution of sodium hydrogencarbonate and water
  7. dry with materialdried over magnesium sulfate
  8. distillationAfter distilling off the solvent
  9. customthe obtained oily residue was purified by column chromatography (silica gel, hexane : ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a6bb4fc134424129b23dbc5430738b0b
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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