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

HRID 658826노트

반응식

HRID 658826 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ef2323d0fe7544779feb9d5db5c4759b
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076516B2

반응 노트

불러오는 중…