Sodium borohydride → (5,6-Dimethoxy-3-(4-methyloxyphenoxy)-benzo[b]thiophen-2-yl)methanol

HRID 1004124

Reaction equation

HRID 1004124 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[C:24]([O:25][CH3:26])=[CH:23][C:8]2[S:9][C:10]([CH:21]=[O:22])=[C:11]([O:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:7]=2[CH:6]=1>CO>[CH3:3][O:4][C:5]1[C:24]([O:25][CH3:26])=[CH:23][C:8]2[S:9][C:10]([CH2:21][OH:22])=[C:11]([O:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 110892155,6-Dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophene-2-carbaldehyde

Product 1

HCID 18794388(5,6-Dimethoxy-3-(4-methyloxyphenoxy)-benzo[b]thiophen-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

26 mmol of NaBH4 are added at room temperature to a solution of 24 mmol of the compound obtained in Step E of Example 1 in 100 ml of methanol. After 2 hours' reaction, one equivalent of NaBH4 is added to the reaction mixture. After 12 hours' reaction, the solution is concentrated and then diluted with ethyl acetate, washed with a 1N HCl solution, then with water and then with a saturated NaCl solution, subsequently dried over calcium sulphate, filtered and concentrated under reduced pressure. Chromatography over silica gel (dichloromethane/ethyl acetate: 95/5) enables 6.07 g of the expected product to be isolated.

Workup

  1. additionis added to the reaction mixture
  2. customAfter 12 hours' reaction
  3. concentrationthe solution is concentrated
  4. additiondiluted with ethyl acetate
  5. washwashed with a 1N HCl solution
  6. dry with materialwith water and then with a saturated NaCl solution, subsequently dried over calcium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto be isolated

Sources & evidence

ORD record
ord-08dee4bf16114f4c80b7e9503bbda772
Source dataset
uspto-grants-2000_04
Patent number
US06048875

Linked notes

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