Boron trifluoride etherate → 178167-77-6

HRID 2287457ノート

反応式

HRID 2287457 の反応式
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].B(F)(F)F.CCOCC.[CH3:19][C:20]1([CH:26]=[CH2:27])[O:25][C:23](=[O:24])[CH2:22][CH2:21]1>O1CCOCC1.CCOCC>[CH3:19][C:20]1([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:26][CH2:27][C:4]2[C:3](=[C:2]([CH3:1])[C:7]([CH3:8])=[CH:6][CH:5]=2)[O:9]1

参加物

6

反応物 3

HCID 8000Boron trifluoride etherateHCID 106872,3-DimethylphenolHCID 1025504-HYDROXY-4-METHYL-5-HEXENOIC ACID gamma LACTONE

生成物 1

HCID 15887183178167-77-6

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

To a solution of 2,3-dimethylphenol (0.01 mol) and boron trifluoride diethyl etherate (0.016 mol) in dioxane (10 mL, dried on sodium) in a flask was added γ-methyl-γ-vinylbutyrolactone (0.016 mol) in dioxane (5.0 mL) via syringe pump over 50 min at 110° C. (oil bath, reflux) under nitrogen. The reaction mixture was cooled to room temperature and diluted with ether (200 mL), then washed with water (100 mL, 2×50 mL) and dried over sodium sulfate. Ether was then removed in vacuum. The residue was dissolved in methanol (30 mL), and solvent was removed in vacuum. The reaction mixture was purified by flash column chromatography on silica gel (eluent ethyl acetate/hexane, 1:1). Fractions containing the desired chroman were pooled, solvent was removed, and the compound was crystallized from ethyl acetate/hexane. M.P.: 93-94° C.

後処理

  1. temperature(oil bath, reflux) under nitrogen
  2. washwashed with water (100 mL, 2×50 mL)
  3. dry with materialdried over sodium sulfate
  4. customEther was then removed in vacuum
  5. dissolutionThe residue was dissolved in methanol (30 mL)
  6. customsolvent was removed in vacuum
  7. customThe reaction mixture was purified by flash column chromatography on silica gel (eluent ethyl acetate/hexane, 1:1)
  8. additionFractions containing the desired chroman
  9. customsolvent was removed
  10. customthe compound was crystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-3da906a38c1847e48b8d9d4c2bf41b4e
出典データセット
uspto-grants-2000_07
特許番号
US06083982

反応ノート

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