Potassium Carbonate → 3,3,3-Triethoxyprop-1-yne

HRID 1868822Notes

Reaction equation

HRID 1868822 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].C([O-])([O-])=O.[K+].[K+]>CO.CCCCC>[CH2:13]([O:12][C:5]([O:6][CH2:7][CH3:8])([O:9][CH2:10][CH3:11])[C:4]#[CH:3])[CH3:14]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 11459211Silane, trimethyl(3,3,3-triethoxy-1-propynyl)-

Product 1

HCID 109209723,3,3-Triethoxyprop-1-yneYield 75.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8003PentaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of trimethyl(3,3,3-triethoxyprop-1-ynyl)silane (25 g, 102 mmol) in MeOH (400 mL), was treated with K2CO3 (14 g, 102 mmol). The reaction was stirred at 23° C. After 15 hours, the reaction was diluted with pentane (500 mL). The pentane layer was separated, and the MeOH layer was extracted with pentane (2×250 mL). The combined pentane layers were washed with water (200 mL), dried over MgSO4, and concentrated (at 220 torr on rotary evaporator). The crude product was filtered through a silica gel plug using 10% diethyl ether/pentane as the eluant and concentrated (at 220 torr on rotary evaporator) affording 13.25 g of 3,3,3-triethoxyprop-1-yne.

Workup

  1. customThe pentane layer was separated
  2. extractionthe MeOH layer was extracted with pentane (2×250 mL)
  3. washThe combined pentane layers were washed with water (200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custom(at 220 torr on rotary evaporator)
  7. filtrationThe crude product was filtered through a silica gel plug
  8. concentrationconcentrated
  9. custom(at 220 torr on rotary evaporator)

Sources & evidence

ORD record
ord-d96dfbf33e3d4c769f14645b3895700c
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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