Hydrochloric Acid → 3-Methyl-1-(2-methyl-5-phenylfuran-3-yl)butan-1-ol

HRID 1877061노트

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HRID 1877061 반응식
[CH3:1][CH:2]1[CH:6]=[CH:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(C=O)[O:3]1.[CH:15]1([Mg]Br)CCC1.[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.Cl.O>O1CCCC1>[CH3:22][CH:23]([CH3:15])[CH2:24][CH:25]([C:6]1[CH:5]=[C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:3][C:2]=1[CH3:1])[OH:21]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 866463722-Methyl-5-phenylfuran-5-carbaldehydeHCID 178420629HCID 178420629, 화합물

생성물 1

HCID 685095783-Methyl-1-(2-methyl-5-phenylfuran-3-yl)butan-1-ol수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 2-methyl-5-phenylfuran-5-carbaldehyde (1.3 g) in tetrahydrofuran (30 mL) was added dropwise 1N cyclobutylmagnesium bromide-tetrahydrofuran solution (10.5 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 1 hr. The reaction mixture was treated with 1N hydrochloric acid, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (0% ethyl acetate/hexane to 20% ethyl acetate/hexane) to give the title compound (1.5 g, 87%) as a yellow crystal.

후처리

  1. additionafter the completion of the dropwise addition
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column (0% ethyl acetate/hexane to 20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-d3c8801d2bdd42cca3886c9f8fb96d91
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309580B2

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