Ethanol → HCID 19900616, compound

HRID 1029986Notes

Reaction equation

HRID 1029986 reaction equation
[C:1](=[O:47])([O:16][C:17]1[C:18]([CH3:46])=[C:19]2[C:24](=[C:25]([CH3:28])[C:26]=1[CH3:27])[O:23][C:22]([CH3:45])([CH2:29][CH2:30][CH2:31][CH:32]([CH3:44])[CH2:33][CH2:34][CH2:35][CH:36]([CH3:43])[CH2:37][CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])[CH2:21][CH2:20]2)[O:2][CH2:3][CH:4]1[O:15][CH:5]1[CH2:6][O:7]CC1C=CC=CC=1.C(O)C.[H][H]>[C].[Pd].C(O)(=O)C>[C:1](=[O:47])([O:16][C:17]1[C:18]([CH3:46])=[C:19]2[C:24](=[C:25]([CH3:28])[C:26]=1[CH3:27])[O:23][C:22]([CH3:45])([CH2:29][CH2:30][CH2:31][CH:32]([CH3:44])[CH2:33][CH2:34][CH2:35][CH:36]([CH3:43])[CH2:37][CH2:38][CH2:39][CH:40]([CH3:41])[CH3:42])[CH2:21][CH2:20]2)[O:2][CH2:3][CH:4]1[O:15][CH:5]1[CH2:6][OH:7]

Participants

6

Reactant 3

HCID 702EthanolHCID 21685080HCID 21685080, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19900616HCID 19900616, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture comprising 6.5 g (0.01 mol) of 4-benzyloxy-2,3-epoxybutyl 2,5,7,8-tetramethyl-2-(4',8', 12'-trimethyltridecyl)-6-chromanyl carbonate, 1 g of 5% palladium carbon, 150 ml of ethanol and 5 ml of acetic acid was catalytically reduced with hydrogen at an initial pressure 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 1/3, poured into water and extracted with ether. Then the extract was successively washed with an aqueous solution of sodium hydrogencarbonate and water, and dried. After distilling off the solvent, the obtained oily residue was purifed by column chromatography (silica gel, hexane/ethyl acetate) to thereby give 4.5 g of the title compound as a colorless oily product.

Workup

  1. customwas absorbed any more (approximately 6 hours)
  2. filtrationAfter filtering off the catalyst
  3. concentrationthe filtrate was concentrated
  4. additionpoured into water
  5. extractionextracted with ether
  6. washThen the extract was successively washed with an aqueous solution of sodium hydrogencarbonate and water
  7. customdried
  8. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-cc286a999c544059b018024bc1db0ef6
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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