Water → HCID 68798699, compound

HRID 1007946Notes

Reaction equation

HRID 1007946 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([CH:10]=O)=[CH:7][CH:8]=[CH:9][C:2]1=2.O.[C:13]([O:16][CH2:17]C)(=O)C>O1CCCC1>[CH3:13][O:16][CH:17]=[CH:10][C:6]1[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 139857971-Benzothiophene-4-carbaldehyde

Product 1

HCID 68798699HCID 68798699, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

In an atmosphere of nitrogen, 4.85 g of (methoxymethyl)triphenylphosphonium chloride is suspended in 40 mL of tetrahydrofuran. Then, 1.5 mL of diisopropylamine is added to the suspension, and cooled to −60° C. After dropwise adding thereto 6.6 mL of 1.6 mol/L solution of n-butyllithium in hexane, the mixture thus obtained is stirred for 30 minutes at an ice-cooled temperature. Then, the reaction mixture is cooled to −60° C., a solution of 1.72 g of benzo[b]thiophene-4-carboaldehyde in 15 mL of tetrahydrofuran is dropwise added, and the resulting mixture is allowed to stand overnight at ambient temperature. The reaction mixture is introduced into a mixture of water and ethyl acetate, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, the residue is treated with diethyl ether, and the deposited crystal is filtered off. The solvent is distilled off from the filtrate under reduced pressure, and the residue thus obtained is purified by column chromatography (eluent: n-hexane:ethyl acetate=100:1 to 50:1) to obtain 1.04 g of 2-benzo[b]thiophen-4-yl-1-ethenyl methyl ether as an oily product.

Workup

  1. temperaturecooled temperature
  2. customthe organic layer is separated
  3. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. additionthe residue is treated with diethyl ether
  7. filtrationthe deposited crystal is filtered off
  8. distillationThe solvent is distilled off from the filtrate under reduced pressure
  9. customthe residue thus obtained
  10. customis purified by column chromatography (eluent: n-hexane:ethyl acetate=100:1 to 50:1)

Sources & evidence

ORD record
ord-346b0b7d27bd43a1b000a1127e5e134d
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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