Boron tribromide → 4-Cyano-4-(3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran

HRID 1108109

반응식

HRID 1108109 반응식
[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].B(Br)(Br)Br>ClCCl>[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 187863664-(3-Methoxyphenyl)oxane-4-carbonitrile

생성물 1

HCID 112871604-Cyano-4-(3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a dichloromethane (80 ml) solution of 4-cyano-4-(3-methoxyphenyl)-3,4,5,6-tetrahydro-2H-pyran (2.32 g, 10.35 mmol) cooled to 0° C. was added boron tribromide (3.15 ml, 33.3 mmol) dropwise over 10 min. The ice-bath was removed and the reaction mixture stirred at ambient temperature for 19 h, and then at reflux for 4 h. The reaction mixture was cooled and poured into water (150 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml×3). The combined organic extracts were washed with brine (50 ml), dried (MgSO4) and concentrated in vacuo. The crude product was crystallized from isopropyl ether to afford titled compound as off-white solids (1.43 g, 66%).

후처리

  1. customThe ice-bath was removed
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction mixture was cooled
  4. additionpoured into water (150 ml)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (50 ml×3)
  7. washThe combined organic extracts were washed with brine (50 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude product was crystallized from isopropyl ether

출처 및 근거

ORD 기록
ord-331b6100816c4a51b80fe6797b7d89ae
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06063928

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