Sodium borohydride → Benzenemethanol,2-benzo[b]thien-5-yl-

HRID 270013Notes

Reaction equation

HRID 270013 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH:12]=[O:13])[CH:8]=[CH:9][C:2]1=2.[BH4-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH2:12][OH:13])[CH:8]=[CH:9][C:2]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 60139760Benzaldehyde,2-benzo[b]thien-5-yl-

Product 1

HCID 60139743Benzenemethanol,2-benzo[b]thien-5-yl-Yield 93.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-Benzo[b]thiophene-5-yl-benzaldehyde (compound PRE14) (3.31 g, 13.9 mmole) in methanol (30 mL) was added at 0-5° C. portionwise NaBH4 (0.528 g, 13.9 mmole). At the end of the addition, the cooling bath was removed and the reaction mixture was stirred at room temperature for 2 h. After concentration, the residue was diluted with water and diethyl ether, the organic layer dried over Na2SO4 and concentrated to give 3.13 g of compound O7 as an orange brown oil (Yield=94%).

Workup

  1. additionAt the end of the addition
  2. customthe cooling bath was removed
  3. concentrationAfter concentration
  4. additionthe residue was diluted with water and diethyl ether
  5. dry with materialthe organic layer dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-019cd25709ee4712a39f89c9e7b44b58
Source dataset
uspto-grants-2008_11
Patent number
US07449481B2

Reaction notes

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