Water → Diethyl 2-[(2,5-dichloro-3-thienyl)methyl]malonate

HRID 1004169노트

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HRID 1004169 반응식
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][C:16]1[CH:20]=[C:19]([Cl:21])[S:18][C:17]=1[Cl:22].O>CN(C=O)C.C1COCC1>[Cl:22][C:17]1[S:18][C:19]([Cl:21])=[CH:20][C:16]=1[CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10]

참가 물질

7

반응물 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 234340823-(Bromomethyl)-2,5-dichlorothiophene

생성물 1

HCID 23434141Diethyl 2-[(2,5-dichloro-3-thienyl)methyl]malonate수율 80%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a stirred solution of sodium hydride (60% oil dispersion, 7.6 g, 190 mmol) in DMF (32 mL) was added a solution of diethyl malonate (35.2 g, 220 mmol) in THF (120 mL) at 0° C. and the mixture was stirred for 30 min at 0° C. To the mixture was added a solution of 3-(bromomethyl)-2,5-dichlorothiophene (26.9 g, 110 mmol) in THF (50 mL) at -35° C. over 1.5 hours. After stirring at -35° C. for 2 hours, the reaction mixture was poured into water and the whole extracted with ethyl acetate (200 mL×3). The combined organic layer was washed with water (200 mL), brine (200 mL), dried over MgSO4 and concentrated in vacuo. Fractionally distillation of the residue under reduced pressure (bp 150° C., 1.0 mmHg) provided the subtitle compound (28.6 g, 80% yield).

후처리

  1. stirringAfter stirring at -35° C. for 2 hours
  2. extractionthe whole extracted with ethyl acetate (200 mL×3)
  3. washThe combined organic layer was washed with water (200 mL), brine (200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. distillationFractionally distillation of the residue under reduced pressure (bp 150° C., 1.0 mmHg)

출처 및 근거

ORD 기록
ord-a440ad4640e943ff8bd261ddcf140336
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048880

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