Hydrochloric Acid → 2,3-Dimethyl-4-(2,2,3-trimethylcyclopent-3-enyl)butanal

HRID 583622

반응식

HRID 583622 반응식
[CH3:1][Mg]Br.[CH3:4][C:5](=[CH:8][CH2:9][CH:10]1[CH2:14][CH:13]=[C:12]([CH3:15])[C:11]1([CH3:17])[CH3:16])[CH:6]=[O:7].Cl>C(OCC)C>[CH3:4][CH:5]([CH:8]([CH3:1])[CH2:9][CH:10]1[CH2:14][CH:13]=[C:12]([CH3:15])[C:11]1([CH3:17])[CH3:16])[CH:6]=[O:7]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 30175572-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enalHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 154310452,3-Dimethyl-4-(2,2,3-trimethylcyclopent-3-enyl)butanal수율 50.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

100 ml (0.30 mol) of methylmagnesium bromide solution in diethyl ether was added to 60.0 g (0.32 mol) of cuprous iodide suspended in 350 ml of the same solvent at -10° C., followed by addition of 52.0 g (0.27 mol) of 2-methyl-4-(2,2,3-trimethylcyclopent-3-enyl)but-2-enal dissolved in 300 ml of anhydrous diethyl ether at 0° C. and stirring at the same temperature was continued for 0.5 hours. The reaction mixture was treated with 200 ml of 1.0 N hydrochloric acid, decanted and the organic layer was washed with 2×300 ml of brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluent: hexane/MTBE 15:1) to give 28.2 g (50% yield) of 2,3-dimethyl-4-(2,2,3-trimethylcyclopent-3-enyl)butanal.

후처리

  1. customdecanted
  2. washthe organic layer was washed with 2×300 ml of brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (eluent: hexane/MTBE 15:1)

출처 및 근거

ORD 기록
ord-9e66560732a1403ebe832736d1a0a33b
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929291

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