Methanol → 4-Ethynylbenzaldehyde

HRID 2262333Notes

Reaction equation

HRID 2262333 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)(C)C.CO.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:6]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)#[CH:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 27716434-(Trimethylsilylethynyl)benzaldehyde

Product 1

HCID 27716454-EthynylbenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As shown in the following Reaction 7, 250 mg (1.19 mmol) of 4-trimethylsilylethynyl benzaldehyde obtained in A of Example 1-2 was melted in 10 mL of methylenechloride and 10 mL of methanol at room temperature, and 1.25 g (9.04 mmol, 7.6 eq) of potassium carbonate was added thereto, and then the reaction solution was stirred for 6 hours. Next, the reaction solution was extracted with ether 2 times and with 1M sodium chloride aqueous solution 1 time. The organic solvent layer was dehydrated with magnesium sulfate, filtered, and then distilled under reduced pressure. The compound distilled under reduced pressure was purified with a column chromatography (mobile phase volume ratio; ethylacetate:n-hexane=1:10) to obtain 130 mg of 4-ethynylbenzaldehyde with the yield of 93%. NMR data of the obtained compound is as follows. [1H NMR (400 MHz, CDCl3): δ 10,02 (s, 1H), 7.83 (d, 2H), 7.63 (d, 2H), 3.27 (s, 1H)].

Workup

  1. customobtained in A of Example 1-2
  2. extractionNext, the reaction solution was extracted with ether 2 times and with 1M sodium chloride aqueous solution 1 time
  3. filtrationfiltered
  4. distillationdistilled under reduced pressure
  5. distillationThe compound distilled under reduced pressure
  6. customwas purified with a column chromatography (mobile phase volume ratio; ethylacetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-9765f58b3c3a47a48ce3ca47f2c085d5
Source dataset
uspto-grants-2010_12
Patent number
US07850872B2

Reaction notes

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