Ethanol → HCID 68646365, compound

HRID 339622Notes

Reaction equation

HRID 339622 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].[CH3:22]CO>>[Br:3][C:4]1[C:11]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH3:22])=[CH:18][CH:19]=2)=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7]

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 59515212HCID 59515212, compound

Product 1

HCID 68646365HCID 68646365, compound

Conditions

Temperature
0 °C

Procedure

NaBH4 (0.38 g, 10 mmol) was added to a solution of 2-bromo-3-(4-methoxy-benzyloxy)-benzaldehyde (1.59 g, 4.95 mmol) in EtOH (15 mL) at 0° C. (bath temp). The mixture was stirred at 0° C. (bath temp) for 1.5 h and then concentrated in vacuo. H2O (10 mL) was added and the aqueous layer was extracted with EtOAc (2×50 mL). The organic fractions were washed with brine (20 mL), dried (Na2SO4), and concentrated in vacuo to give the title compound as white solid: yield 1.50 g (94%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionH2O (10 mL) was added
  3. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washThe organic fractions were washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47b5de9a5ee9449a8d3e23afd7c54fd1
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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