Hydrochloric Acid → Cyclopentyl(2-methyl-5-phenylfuran-3-yl)methanol

HRID 1877065

반응식

HRID 1877065 반응식
[CH3:1][C:2]1[O:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]=[O:8].[CH:15]1([Mg]Br)[CH2:19][CH2:18][CH2:17][CH2:16]1.O1CCCC1.Cl.O>O1CCCC1>[CH:15]1([CH:7]([C:6]2[CH:5]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:3][C:2]=2[CH3:1])[OH:8])[CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27953132-Methyl-5-phenyl-3-furaldehydeHCID 178420631HCID 178420631, 화합물

생성물 1

HCID 68509772Cyclopentyl(2-methyl-5-phenylfuran-3-yl)methanol수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-methyl-5-phenylfuran-3-carbaldehyde (1.3 g) in tetrahydrofuran (30 mL) was added dropwise 1N cyclopentylmagnesium 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 (0.9 g, 50%) as a white 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-a8276d17bb724d308ae31027f498924f
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309580B2

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