Bromide ion → 3-(3-Methoxyphenyl)-3-hydroxyindan-1-one

HRID 464687

반응식

HRID 464687 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[Br-].[Mg].[C:13]1(=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[CH2:14]1>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2([OH:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH2:14]2)[CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 259Bromide ionHCID 118151,3-IndandioneHCID 5462224MagnesiumHCID 178490745HCID 178490745, 화합물

생성물 1

HCID 202624453-(3-Methoxyphenyl)-3-hydroxyindan-1-one수율 59%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

m-Methoxyphenyl magnesium bromide (prepared from 10 g of the corresponding bromide and 1.45 g of magnesium turnings in ether) was treated at 0° with a solution of 1,3-indandione (3.5 g) in ether. After stirring at 25° for 4.5 hours, the mixture was quenched with saturated ammonium chloride solution. The layers were separated, the aqueous layer was extracted with ether, and the organic layers were dried (MgSO4) and concentrated. Chromatography of the residue on silica gel provided the title compound as a viscous yellow oil (3.6 g, 59%). NMR and IR spectra were consistent with the assigned structure.

후처리

  1. customthe mixture was quenched with saturated ammonium chloride solution
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ether
  4. dry with materialthe organic layers were dried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6cf9212a2c7d470bb5088da055a3aa98
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04548946

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