1-Undecyn-3-ol, 1-(trimethylsilyl)- → 1-Undecyn-3-ol

HRID 2081308Notes

Reaction equation

HRID 2081308 reaction equation
C[Si](C)(C)[C:3]#[C:4][CH:5]([OH:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>[OH-].[Na+].CO>[CH:3]#[C:4][CH:5]([OH:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 1

HCID 108900431-Undecyn-3-ol, 1-(trimethylsilyl)-

Product 1

HCID 2477661-Undecyn-3-olYield 92.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

10 g of (3RS)-1-(trimethylsilyl)-1-undecin-3-ol is dissolved in a mixture of 420 ml of 0.1 n sodium hydroxide solution and 420 ml of methanol and stirred for 3 hours at room temperature. Then, the methanol is removed in a vacuum, shaken with diethyl ether, dried (Na2SO4) and concentrated by evaporation. 6.46 g of (3RS)-1-undecin-3-ol is obtained as a yellow oil, which is further reacted as a crude product.

Workup

  1. customThen, the methanol is removed in a vacuum
  2. stirringshaken with diethyl ether
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2eb0498c37054905bbf74437d84afe6c
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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