Potassium Hydroxide → 3-(3-Ethynylphenyl)propan-1-ol

HRID 658826ノート

反応式

HRID 658826 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:11]#[C:12]C(C)(O)C)[CH:8]=[CH:9][CH:10]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[C:11]([C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:10]=[CH:9][CH:8]=1)#[CH:12]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 576085154-(3-(3-Hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol

生成物 1

HCID 576083943-(3-Ethynylphenyl)propan-1-ol

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 4-(3-(3-hydroxypropyl)phenyl)-2-methylbut-3-yn-2-ol (49) (0.750 g, 3.4 mmol) in toluene (50 mL) was added powdered KOH (0.390 g, 7 mmol). The resulting mixture was heated at reflux for 45 min. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure to 10-15 mL volume and partitioned between EtOAc and water. The combined organics were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (15% EtOAc-hexanes) gave 3-(3-ethynylphenyl)propan-1-ol (50) as a light brown oil. Yield (0.272 g, 49%).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 45 min
  3. concentrationthe reaction mixture was concentrated under reduced pressure to 10-15 mL volume
  4. custompartitioned between EtOAc and water
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography (15% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-ef2323d0fe7544779feb9d5db5c4759b
出典データセット
uspto-grants-2011_12
特許番号
US08076516B2

反応ノート

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