HCID 11013136, compound → (5S)-6-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-methyl-1-hexanol

HRID 2378491Notes

Reaction equation

HRID 2378491 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH3:23])[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[C:19]([Si:16]([CH3:18])([CH3:17])[O:15][CH2:14][C@@H:13]([CH3:23])[CH2:12][CH2:11][CH2:10][CH2:9][OH:8])([CH3:21])([CH3:22])[CH3:20]

Participants

4

Reactant 1

HCID 11013136HCID 11013136, compound

Product 1

HCID 10933803(5S)-6-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-methyl-1-hexanolYield 100.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 64.0 g (0.19 mol) of the benzylether VIII in 500 ml of THF was hydrogenated (3.5 bar) over 7.0 g of 20% Pd(OH)2/C for 30 min at ambient temperature. The catalyst was removed by filtration and the filtrate was concentrated to afford alcohol IX as colorless oil (46.9 g, 100%). Rf=0.33 (SiO2, 1:1 heptane-TBME).

Workup

  1. customfor 30 min
  2. customat ambient temperature
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-eb8685b4b890481db2689f40765bc50c
Source dataset
uspto-grants-2008_12
Patent number
US07470792B2

Reaction notes

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