Potassium Carbonate → HCID 118588387, compound

HRID 928879Notes

Reaction equation

HRID 928879 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:22]=[CH:21][C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:12])=[CH:9][CH:8]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CO>[C:6]([C:7]1[CH:22]=[CH:21][C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:12])=[CH:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 90349595HCID 90349595, compound

Product 1

HCID 118588387HCID 118588387, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Heptyl 4-[(trimethylsilyl)ethynyl]benzoate (3a) (10.4 g, 32.8 mmol) was dissolved in tetrahydrofuran/methanol (3/1, v/v) (400 mL), potassium carbonate (1.00 g, 7.24 mmol) was added, and the mixture was stirred at −10° C. for 1 hr. The reaction solvent was concentrated, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (ethyl acetate:hexane=1:25) to give heptyl 4-ethynylbenzoate (4a) (6.58 g, yield 82%) as an oily liquid.

Workup

  1. concentrationThe reaction solvent was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography (ethyl acetate:hexane=1:25)

Sources & evidence

ORD record
ord-53a4bafe931c423bb4758473d3503875
Source dataset
uspto-grants-2016_03
Patent number
US09290592B2

Reaction notes

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