Ethanol → 1-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methoxyethanol

HRID 1881875Notes

Reaction equation

HRID 1881875 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([C:11](=[O:15])[CH2:12][O:13][CH3:14])=[CH:9][N:10]=1.O1CCCC1.C(O)C.[BH4-].[Na+]>O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:15])[CH2:12][O:13][CH3:14])=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 593312511-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methoxyethanone

Product 1

HCID 593313571-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methoxyethanolYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]-2-methoxyethanone (2.00 g) in a mixed solvent of tetrahydrofuran (10 mL) and ethanol (10 mL) was slowly added sodium borohydride (0.18 g) at 0° C., and the mixture was stirred at room temperature 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, the title compound (1.84 g, yield 91%) was obtained as a colorless oil from a fraction eluted with ethyl acetate. MS: 232 (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-96cd90606cdc48d8aa67f57257ef97c3
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…