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

HRID 1418499

反応式

HRID 1418499 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1971f387252f422bb3176677c9bfffff
出典データセット
uspto-grants-1999_03
特許番号
US05883106

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