Water → 1H-Inden-1-one, 2,3-dihydro-2-(hydroxymethylene)-

HRID 366381

반응식

HRID 366381 반응식
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH:13](OCC)=[O:14].O>C1(C)C=CC=CC=1>[OH:14][CH:13]=[C:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:10]

참가 물질

6

반응물 4

HCID 962WaterHCID 67351-IndanoneHCID 8025Ethyl formateHCID 24758Sodium hydride

생성물 1

HCID 37648821H-Inden-1-one, 2,3-dihydro-2-(hydroxymethylene)-

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

1-Indanone (Aldrich) (5.0 g, 37.8 mmol) in toluene (25 cm3) was added dropwise, to a stirring solution of sodium hydride (Aldrich) (1.8 g, 45.4 mmol 60% w/w dispersion in oil), ethyl formate (Aldrich) (5.6 g, 75.6 mmol) and toluene (50 cm3), under nitrogen, at 0° C. The reaction was stirred for 17 hours before adding water (50 cm3). The organic layer was washed with water and 2M NaOH. The combined aqueous extracts were acidified with 10 M HCl and the precipitate extracted with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford a yellow-orange solid. An analytically pure sample was obtained by Kugelrohr distillation (0.01 mmHg/100° C.) to give a yellow solid m.p. 110-112° C.

후처리

  1. washThe organic layer was washed with water and 2M NaOH
  2. extractionthe precipitate extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow-orange solid
  7. customAn analytically pure sample was obtained by Kugelrohr distillation (0.01 mmHg/100° C.)

출처 및 근거

ORD 기록
ord-790913db6aae4f30bc155fe71369a1ef
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130228

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