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

HRID 1877061ノート

反応式

HRID 1877061 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 866463722-Methyl-5-phenylfuran-5-carbaldehydeHCID 178420629HCID 178420629、化合物

生成物 1

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

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-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.

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-d3c8801d2bdd42cca3886c9f8fb96d91
出典データセット
uspto-grants-2012_11
特許番号
US08309580B2

反応ノート

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