Sodium borohydride → [3-(Cyclopropylmethoxy)phenyl]methanol

HRID 1006244Notes

Reaction equation

HRID 1006244 reaction equation
[BH4-].[Na+].[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])[CH2:5][CH2:4]1>CO>[OH:12][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:7][CH2:6][CH:3]2[CH2:5][CH2:4]2)[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 220482703-(Cyclopropylmethoxy)benzaldehyde

Product 1

HCID 22676783[3-(Cyclopropylmethoxy)phenyl]methanolYield 89.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.75 g, 20 mmol) was added in portions to a stirred solution of 3-(cyclopropylmethoxy)benzaldehyde (Lit: Chem. Pharm. Bull. 1975, 23, 2878) (3.5 g, 20 mmol) in methanol (80 mL). The mixture was stirred for 2 h and then quenched with water (300 mL). The product was extracted with ethyl acetate (3×150 mL) and then the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to leave 3.2 g (89%) of crude product. This material was used in the next reaction without further purification or analysis.

Workup

  1. customquenched with water (300 mL)
  2. extractionThe product was extracted with ethyl acetate (3×150 mL)
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-033b87ce59c14cb692d82a2d022a6a29
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

Loading…