Sodium Hydroxide → 3,3,3-Triethoxyprop-1-yne

HRID 24029Notes

Reaction equation

HRID 24029 reaction equation
[OH-].[Na+].C[Si](C)(C)[C:5]#[C:6][C:7]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10]>O.C(O)C>[CH2:15]([O:14][C:7]([O:8][CH2:9][CH3:10])([O:11][CH2:12][CH3:13])[C:6]#[CH:5])[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11459211Silane, trimethyl(3,3,3-triethoxy-1-propynyl)-

Product 1

HCID 109209723,3,3-Triethoxyprop-1-yneYield 55.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (0.14 g, 3.60 mmol) in water (50 mL) was added to a solution of trimethyl-triethoxyprop-1-ynyl-silane (50.0 g, 208 mmol) in ethanol (250 mL). After stirring for 1 hour at room temperature, water was added and the mixture was extracted with ethyl acetate. The organic extracts were dried with magnesium sulfate and the solvent was removed under reduced pressure to give the title compound (20.0 g, 52% yield) as yellow oil. 1H NMR (CDCl3) δ 3.70 (q, 6H, J=8.0 Hz), 2.56 (s, 1H) 1.24 (t, 9H, J=8.0 Hz).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic extracts were dried with magnesium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c8f25159d90e4307b33f2a65cecd66cb
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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