Water → [2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]methanol

HRID 1881878Notes

Reaction equation

HRID 1881878 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([CH:11]=[O:12])=[CH:9][N:10]=1.[BH4-].[Na+].O>CO>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH2:11][OH:12])=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 593313182-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde

Product 1

HCID 59331528[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]methanolYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde (7.00 g) in methanol (30 mL) was slowly added sodium borohydride (0.53 g) at 0° C., and the mixture was stirred at 0° C. for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (6.59 g, yield 93%) was obtained as a colorless oil from a fraction eluted with ethyl acetate. MS: 188 (MH+).

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82af796e31044b2a98260b425c46b84d
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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