Sodium borohydride → 1-(3-Acetylamino-4-methoxyphenyl)-2-propyl Alcohol

HRID 2179892Notes

Reaction equation

HRID 2179892 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH2:13][C:14](=[O:16])[CH3:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH2:13][CH:14]([OH:16])[CH3:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 697335313-Acetylamino-4-methoxyphenylacetone

Product 1

HCID 697337221-(3-Acetylamino-4-methoxyphenyl)-2-propyl AlcoholYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 12 (0.25 g, 1.13 mmol) in methanol was added NaBH4 in portions in the period of 20 min at 0° C. The resulting solution was stirred at such temperature for another 40 min. No more starting materials were detected on TLC. Ice water was added to the reaction slowly. It was extracted with CHCl3 three times. The combined organic phases were washed with brine, and dried over Na2SO4. Removal of the solvent afforded the crude product. Purification of the crude product by using a silica gel column gave the desired product 13 (0.24 g, 95%). 1HNMR(CDCl3): 8.24 (d, J=1.8 Hz, 1H), 7.75 (br, 1H), 6.82 (m, 2H), 4.00 (m, 1H), 3.86 (s, 3H), 2.70 (m, 2H), 2.20 (s, 3H), 1.24 (d, J=6.1 Hz, 3H).

Workup

  1. extractionIt was extracted with CHCl3 three times
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent
  5. customafforded the crude product
  6. customPurification of the crude product

Sources & evidence

ORD record
ord-9f92f7e210094c56ad03269fc30f567d
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

Loading…