Sodium borohydride → HCID 22851377, compound

HRID 1464482Notes

Reaction equation

HRID 1464482 reaction equation
[O:1]=[CH:2][C@@H:3]([O:8][CH3:9])[O:4][CH2:5][CH:6]=[O:7].[BH4-].[Na+]>O.CO>[OH:1][CH2:2][C@@H:3]([O:8][CH3:9])[O:4][CH2:5][CH2:6][OH:7]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22851381(2S)-Methoxy(2-oxoethoxy)acetaldehyde

Product 1

HCID 22851377HCID 22851377, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1,5-dioxo-2(S)-methoxy-3-oxa-pentane (D4) (1.5 g, 11 mmole), prepared as described in "Methods on Carbohydrate Chemistry" Acad. Press., Vol. 1, 445, (1962), was dissolved in a mixture of water (10 ml) and methanol (10 ml) and treated with sodiumborohydride (0.1 g) dissolved in water (2 ml). After 20 minutes the solution was brought to pH 7 with an acidic resin Dowex 50WX2, filtered off and the solvent was removed under reduced pressure to give 1.4 g (Yield 93%) of the title compound. TLC on Kieselgel Plate F254 (Merck), eluting system methylene chloride:methanol (10:1 by volume) brown spot at Rf =0.24 after heating the TLC plate previously sprayed with sulforic acid.

Workup

  1. filtrationfiltered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-29f2b523ba7b45a1a18eba629b6db255
Source dataset
uspto-grants-1994_04
Patent number
US05304687

Reaction notes

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