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Sulfoxonium, trimethyl-, iodide (1:1) → (3-(Benzyloxy)phenyl)(2-methylcyclopropyl)methanone

HRID 1662570
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HRID 1662570 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:19])/[CH:16]=[CH:17]/[CH3:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[CH3:21][S+](C)(C)=O.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH:16]2[CH2:18][CH:17]2[CH3:21])=[O:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57706211(E)-1-(3-(Benzyloxy)phenyl)but-2-en-1-one

생성물 1

HCID 57706540(3-(Benzyloxy)phenyl)(2-methylcyclopropyl)methanone수율 36.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
60 °C

실험 절차

To a solution of 93.C (5.33 g, 21.1 mmol) in ACN (200 mL) were added trimethylsulfoxonium iodide (available from Aldrich) (5.58 g, 25.3 mmol) and DBU (4.11 mL, 27.5 mmol). The mixture was stirred overnight at 60° C. under N2, cooled to room temperature, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 93.D (2.04 g, 36% yield) as a colorless oil.

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-73e4047b6c164f9caaee95197e9161f1
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030354B2

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