5-Chloro-1-indanone → HCID 58392088, 화합물

HRID 561443

반응식

HRID 561443 반응식
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][CH2:23][C:24]2=[O:27])=[CH:20][CH:19]=1>O1CCCC1.C(OCC)C>[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH:1]1[CH2:3][CH2:2]1)([OH:16])[CH2:11][CH2:10]2.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][CH2:23][C:24]2([CH:1]2[CH2:3][CH2:2]2)[OH:27])=[CH:20][CH:19]=1

참가 물질

7

반응물 3

HCID 1425995-Chloro-1-indanoneHCID 51007056-Chloro-1-indanoneHCID 178418630HCID 178418630, 화합물

생성물 2

HCID 58392088HCID 58392088, 화합물HCID 58392268HCID 58392268, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

45 ml (22.5 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were added to 2.50 g (15.0 mmol) of a mixture of 5-chloro-2,3-dihydro-1H-inden-1-one and 6-chloro-2,3-dihydro-1H-inden-1-one in 56 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 71.0 mg (2% of theory) of a mixture of 5-chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-ol and 6-chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-ol.

후처리

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-7475267fb2554cbbba68f9a98a747938
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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