Tetrahydrofuran → 2-(1,3-Dioxolan-2-yl)-5-[(2-methoxyethoxy)methyl]-1,3-thiazole

HRID 1881879Notes

Reaction equation

HRID 1881879 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([CH2:11][OH:12])=[CH:9][N:10]=1.Br[CH2:14][CH2:15][O:16][CH3:17].O1CCCC1.[H-].[Na+]>O.CN(C)C(=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH2:11][O:12][CH2:14][CH2:15][O:16][CH3:17])=[CH:9][N:10]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 59331528[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]methanol

Product 1

HCID 593316232-(1,3-Dioxolan-2-yl)-5-[(2-methoxyethoxy)methyl]-1,3-thiazoleYield 29.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a mixture of [2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]methanol (1.02 g), 1-bromo-2-methoxyethane (1.14 g), tetrahydrofuran (6 mL) and N,N-dimethylacetamide (6 mL) was slowly added sodium hydride (60%, oil, 0.28 g) at 0° C. The reaction mixture was stirred at room temperature overnight, water was added, 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 basic silica gel column chromatography, and the title compound (0.40 g, yield 29%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). MS: 246 (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-8c8f1ea78ea841b4b56a27684f7da514
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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