1-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-ol → 1-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one

HRID 460287노트

반응식

HRID 460287 반응식
[CH3:1][C:2]1([CH3:16])[C:6]2[CH:7]=[C:8]([CH:11]([OH:15])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:16][C:2]1([CH3:1])[C:6]2[CH:7]=[C:8]([C:11](=[O:15])[CH:12]([CH3:13])[CH3:14])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

참가 물질

4

반응물 2

HCID 220414081-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-olHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 184453861-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one수율 47.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-ol (example 1e) (1.13 g, 5.15 mmol) in dry dichloromethane (20 mL) was added at room temperature pyridinium chlorochromate (1.33 g, 6.18 mmol). The reaction mixture was stirred for 2 hours at room temperature then filtered over celite. Water was added and the layers separated. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (5% ethyl acetate in hexane) to give 530 mg of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one (47%). 1H NMR (300 MHz; CDCl3): δ 1.21 (d, J=7.2 Hz, 6H), 1.38 (s, 6H), 3.52 (m, 1H), 4.32 (s, 2H), 6.80 (d, J=7.5 Hz, 1H), 7.80 (m, 2H).

후처리

  1. filtrationthen filtered over celite
  2. additionWater was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted twice with dichloromethane
  5. washThe combined organic layers were washed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica gel (5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-4ee1845e7ec34b2bb2ce89108b562057
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196108B2

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