Sodium borohydride → HCID 53916412, compound

HRID 2417415Notes

Reaction equation

HRID 2417415 reaction equation
[O:1]1[C@H:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:8]([CH:20]=[O:21])[CH:7]=2)[CH2:2]1.[BH4-].[Na+]>CO>[O:1]1[C@H:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:8]([CH2:20][OH:21])[CH:7]=2)[CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86591187HCID 86591187, compound

Product 1

HCID 53916412HCID 53916412, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled solution of (2S)-1,2-epoxy-3-(3-formyl-4-benzyloxyphenoxy)propane (2.6 g) in methanol (30 ml) was added sodium borohydride (381 mg). The mixture was stirred at the same temperature for 1 hour and partitioned between chloroform and saturated sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated to give (2S)-1,2-epoxy-3-(3-hydroxymethyl-4-benzyloxyphenoxy)propane (2.57 g) as a yellow oil.

Workup

  1. custompartitioned between chloroform and saturated sodium bicarbonate solution
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7fbb57372a854f49985500cda64c66a4
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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