HCID 19900598, compound → HCID 19900595, compound

HRID 1029989Notes

Reaction equation

HRID 1029989 reaction equation
[C:1](=[O:49])([O:18][C:19]1[C:20]([CH3:48])=[C:21]2[C:26](=[C:27]([CH3:30])[C:28]=1[CH3:29])[O:25][C:24]([CH3:47])([CH2:31][CH2:32][CH2:33][CH:34]([CH3:46])[CH2:35][CH2:36][CH2:37][CH:38]([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:23][CH2:22]2)[O:2][CH2:3][C:4]1([CH2:16][OH:17])[CH2:9][O:8]C(C2C=CC=CC=2)[O:6][CH2:5]1>C(O)(=O)C.[C].[Pd]>[C:1](=[O:49])([O:18][C:19]1[C:20]([CH3:48])=[C:21]2[C:26](=[C:27]([CH3:30])[C:28]=1[CH3:29])[O:25][C:24]([CH3:47])([CH2:31][CH2:32][CH2:33][CH:34]([CH3:46])[CH2:35][CH2:36][CH2:37][CH:38]([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:43])[CH3:44])[CH2:23][CH2:22]2)[O:2][CH2:3][C:4]([CH2:9][OH:8])([CH2:16][OH:17])[CH2:5][OH:6]

Participants

4

Reactant 1

HCID 19900598HCID 19900598, compound

Product 1

HCID 19900595HCID 19900595, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

5.3 g of 5-hydroxymethyl-2-phenyl-1,3-dioxan-5-ylmethyl 2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanyl carbonate was dissolved in 50 ml of acetic acid. To the obtained solution was added 0.3 g of 10% palladium carbon. Then the mixture was catalytically reduced under a hydrogen pressure of 3 kg/cm2. After filtering off the catalyst, the filtrate was poured into water. The oily matter thus precipitated was extracted with ether. The extract was successively washed with water, an aqueous solution of sodium hydrogencarbonate and water, and dried. After distilling off the solvent, 4.5 g of a colorless and resinous product was obtained. It was purified by column chromatography (silica gel, benzene:ethyl acetate=1:1). Thus 3.7 g of the title compound was obtained as a colorless waxy solid.

Workup

  1. filtrationAfter filtering off the catalyst
  2. additionthe filtrate was poured into water
  3. customThe oily matter thus precipitated
  4. extractionwas extracted with ether
  5. washThe extract was successively washed with water
  6. dry with materialan aqueous solution of sodium hydrogencarbonate and water, and dried
  7. distillationAfter distilling off the solvent, 4.5 g of a colorless and resinous product
  8. customwas obtained
  9. customIt was purified by column chromatography (silica gel, benzene:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-650d3de00a2f4c51a9421052f2b068ac
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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