Boron tribromide → HCID 13560308、化合物

HRID 637729ノート

反応式

HRID 637729 の反応式
C[O:2][C:3]1[C:4]([CH:13]=[O:14])=[CH:5][C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]([CH:13]=[O:14])=[CH:5][C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:12]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 10352557HCID 10352557、化合物

生成物 1

HCID 13560308HCID 13560308、化合物収率 67.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 6-methoxy-3,4-dihydrobenzopyran-7-carboxaldehyde (30.00 g, 156 mmol) in dry methylene chloride (625 mL) under nitrogen was cooled to an internal temperature of -67°. A solution of boron tribromide (1M in methylene chloride, 67.5 mL, 67.5 mmol) was added dropwise. The cooling bath was removed and the mixture allowed to stir under nitrogen for three hours. The reaction was then quenched by the dropwise addition of methanol (75 mL) and the resulting mixture poured into saturated aqueous sodium chloride (1200 mL). The layers were separated and the organic extract washed with saturated sodium chloride (600 mL), dried (Na2SO4) and concentrated to a dark solid (31.0 g). Purification by preparative HPLC (Waters Prep 500, 9:1 hexane:ethyl acetate as eluant) afforded 6-hydroxy-3,4-dihydrobenzopyran-7-carboxaldehyde (18.80 g, 67.6%), m.p. 97°-100°.

後処理

  1. customThe cooling bath was removed
  2. customThe reaction was then quenched by the dropwise addition of methanol (75 mL)
  3. additionthe resulting mixture poured into saturated aqueous sodium chloride (1200 mL)
  4. customThe layers were separated
  5. extractionthe organic extract
  6. washwashed with saturated sodium chloride (600 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to a dark solid (31.0 g)
  9. customPurification by preparative HPLC (Waters Prep 500, 9:1 hexane:ethyl acetate as eluant)

出典と根拠

ORDレコード
ord-9c40e516fd304c80b620e78075a047cf
出典データセット
uspto-grants-1985_12
特許番号
US04558067

反応ノート

読み込み中…