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

HRID 1877065

反応式

HRID 1877065 の反応式
[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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27953132-Methyl-5-phenyl-3-furaldehydeHCID 178420631HCID 178420631、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a8276d17bb724d308ae31027f498924f
出典データセット
uspto-grants-2012_11
特許番号
US08309580B2

関連ノート

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