Acetone → HCID 23021542, compound

HRID 501799Notes

Reaction equation

HRID 501799 reaction equation
[CH:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:6]=2[S:5][CH:4]=1)=[O:2].[BH4-].[Na+].CC(C)=O>C(O)C.O1CCCC1>[OH:2][CH2:1][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:6]=2[S:5][CH:4]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 23021519HCID 23021519, compound

Product 1

HCID 23021542HCID 23021542, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.00 g of methyl 3-formyl-1-benzothiophene-7-carboxylate was dissolved in a mixed solution of 15 mL of ethanol and 15 mL of tetrahydrofuran, to which 86 mg of sodium borohydride was added at room temperature, and this solution was stirred for one hour at the same temperature. After acetone was added dropwise to the reaction mixture, from which the solvent was distilled out under reduced pressure, followed by addition of ethyl acetate and water, and this mixture was adjusted to pH 6 with 6M hydrochloric acid, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 0.97 g of methyl 3-(hydroxymethyl)-1-benzothiophene-7-carboxylate as light yellow solid.

Workup

  1. additionwas added at room temperature
  2. distillationwas distilled out under reduced pressure
  3. additionfollowed by addition of ethyl acetate and water
  4. customthe organic phase was separated
  5. washAfter the resultant organic phase was washed with water
  6. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-91cc7b26071045eaa190bd18483de9c6
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

Loading…