1-Bromo-2-Chloroethane → 1-(Carboethoxy)-1-(4-methoxybenzylthio)cyclopropane

HRID 22516

반응식

HRID 22516 반응식
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]([CH2:16][S:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)([O:13][CH2:14][CH3:15])=[O:12].CN1C[CH2:32][CH2:31]N(C)C1=O.BrCCCl>O1CCCC1>[C:11]([C:16]1([S:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:32][CH2:31]1)([O:13][CH2:14][CH3:15])=[O:12]

참가 물질

6

반응물 4

HCID 78491-Bromo-2-ChloroethaneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 108476441-(Carboethoxy)-1-(4-methoxybenzylthio)methaneHCID 57426343Lithium bis(trimethylsilyl)amide2회

생성물 1

HCID 224002171-(Carboethoxy)-1-(4-methoxybenzylthio)cyclopropane수율 21%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Cool lithium hexamethyldisilazane (6 mL of a 1.0M solution in tetrahydrofuran, 6.0 mmol) to -78° C. Add, by cannula transfer, a solution of 1-(carboethoxy)-1-(4-methoxybenzylthio)methane (1.36 g, 5.66 mmol) in tetrahydrofuran (10 mL). Stir for 45 minutes, add 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) (0.73 mL, 6.0 mmol) followed by 1-bromo-2-chloroethane (050 mL, 6.0 mmol) and stir to room temperature overnight. Cool to -78° C., add lithium hexamethyldisilazane (6.0 mL, 6.0 mmol) and stir at room temperature for 24 hours. Quench with saturated ammonium chloride (5 mL) and partition between ethyl acetate (30 mL) and water (30 mL). Separate the organic phase, dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (5:1 hexane/ethyl acetate to 2.5:1 hexane/ethyl acetate) to give 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclopropane (317 mg, 21%).

후처리

  1. additionAdd, by cannula transfer
  2. stirringstir to room temperature overnight
  3. stirringstir at room temperature for 24 hours
  4. customQuench with saturated ammonium chloride (5 mL)
  5. custompartition between ethyl acetate (30 mL) and water (30 mL)
  6. customSeparate the organic phase
  7. dry with materialdry (Na2SO4)
  8. customevaporate the solvent in vacuo
  9. customPurify by chromatography (5:1 hexane/ethyl acetate to 2.5:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-dab25ad53b5e47e6a2206dae9c9bc9f1
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428158

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