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

HRID 1881879노트

반응식

HRID 1881879 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-8c8f1ea78ea841b4b56a27684f7da514
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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