Water → HCID 22666408, compound

HRID 1007943Notes

Reaction equation

HRID 1007943 reaction equation
[F:1][C:2]1[C:3]([CH2:13][C:14](O)=[O:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[O:11][CH3:12].C(OCC)(=O)C.O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[C:3]([CH2:13][CH2:14][OH:15])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 22666473HCID 22666473, compound

Product 1

HCID 22666408HCID 22666408, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 8.1 mL of tetrahydrofuran is dissolved 1.42 g of 2-(6-fluoro-7-methoxybenzo[b]thiophen-5-yl)-acetic acid. At an ice-cooled temperature, 4.8 mL of 1 mol/L solution of borane-tetrahydrofuran complex in tetrahydrofuran is added to the solution obtained above, and the resulting mixture is stirred at ambient temperature for 2 hours. Ethyl acetate and water are added to the reaction mixture, pH is adjusted to 10 with 2 mol/L aqueous solution of sodium hydroxide, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 0.72 g of 2-(6-fluoro-7-methoxybenzo[b]thiophen-5-yl)-1-ethanol is obtained as an oily product.

Workup

  1. additionis added to the solution
  2. customobtained above, and the resulting mixture
  3. customthe organic layer is separated
  4. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-cc56953d51264fbd8515d1357eb5a976
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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