Sodium borohydride → HCID 17755959, compound

HRID 1479252Notes

Reaction equation

HRID 1479252 reaction equation
[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[BH4-].[Na+]>CO.O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH:9]([OH:11])[CH3:10])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 177562771-[4-(Hydroxymethyl)phenoxy]propan-2-one

Product 1

HCID 17755959HCID 17755959, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(4-hydroxymethylphenoxy)-propan-2-one (1.26 g, 6.99 mmol) dissolved in methanol (60 mL) was added solid NaBH4 (0.32 g, 8.39 mmol). After completion of addition the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water, and the aqueous layer was extracted with ethyl acetate (3×). All combined organic layers were dried over Na2SO4, filtered, and concentrated to provide an oil (1.24 g, 6.81 mmol), which was used in the next step without any further purification (98% yield). 1H (CDCl37.29, 600 MHz): δ (2H, d, J=8.4 Hz), 6.90 (2H, d, J=8.5 Hz), 4.62 (2H, s), 4.21 (1H, m), 3.94 (1H, dd, J=9.2, 3.1 Hz), 3.82 (1H, m), 1.29 (3H, d, J=6.4 Hz).

Workup

  1. additionAfter completion of addition the reaction mixture
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  3. dry with materialAll combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5a300ceadea9490db13141f310209f90
Source dataset
uspto-grants-2016_08
Patent number
US09408927B2

Reaction notes

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