Sodium borohydride → 2-(2-(4-Bromophenoxy)ethyl)propane-1,3-diol

HRID 338530Notes

Reaction equation

HRID 338530 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH:9]([C:15](OCC)=[O:16])[C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH:9]([CH2:15][OH:16])[CH2:10][OH:11])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 79459661Diethyl 2-(2-(4-bromophenoxy)ethyl)malonate

Product 1

HCID 794507012-(2-(4-Bromophenoxy)ethyl)propane-1,3-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of diethyl 2-(2-(4-bromophenoxy)ethyl)malonate (2.50 g, 6.96 mmol) in anhydrous MeOH (15 mL) was added sodium borohydride (1.32 g, 34.8 mmol) in portions at 0° C. The reaction mixture was stirred for 30 minutes at this temperature. The reaction mixture was then carefully quenched with water and extracted with ethyl acetate (4×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude product was purified by flash chromatography (ethyl acetate:petroleum ether) to deliver the title compound (1.0 g, 52%) as a white solid.

Workup

  1. customThe reaction mixture was then carefully quenched with water
  2. extractionextracted with ethyl acetate (4×50 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ca80ff7fb78493c9eeb7fd3c639bac8
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

Loading…