Sodium;3-oxidodioxaborirane;tetrahydrate → 3-Cyano-4-{[(1S)-1-methylpropyl]oxy}benzoic acid

HRID 423323ノート

反応式

HRID 423323 の反応式
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:11][C@@H:12]([CH3:15])[CH2:13][CH3:14])=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:2].B1([O-])O[O:17]1.O.O.O.O.[Na+]>C(O)(=O)C>[C:8]([C:7]1[CH:10]=[C:3]([CH:4]=[CH:5][C:6]=1[O:11][C@@H:12]([CH3:15])[CH2:13][CH3:14])[C:1]([OH:17])=[O:2])#[N:9]

参加物

4

反応物 2

HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 866414335-Formyl-2-{[(1S)-1-methylpropyl]oxy}benzonitrile

生成物 1

HCID 666772333-Cyano-4-{[(1S)-1-methylpropyl]oxy}benzoic acid収率 103.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
50 °C

実験手順

To a solution of 5-formyl-2-{[(1S)-1-methylpropyl]oxy}benzonitrile (D35) (220 mg, 1.08 mmol) in acetic acid (20 ml) was added sodium perborate tetrahydrate (334 mg, 2.17 mmol), the reaction mixture was heated at 50° C. over the weekend. The reaction mixture was concentrated in-vacuo. Water (˜50 ml) was added, EtOAc (˜30 ml) was added and the layers partitioned, the aq layer was extracted twice more with EtOAc (˜30 ml) and the combined organics were evaporated to dryness under reduced pressure to give the title compound (245 mg) as an off white solid. δH (d6-DMSO, 400 MHz): 8.17 (2H, apparent d), 7.39 (1H, s), 4.68-4.74 (1H, m), 1.55-1.76 (2H, m), 1.31 (3H, d), 0.95 (3H, t). MS (ES): C12H13NO2 requires 219; found 220 (MH+).

後処理

  1. concentrationThe reaction mixture was concentrated in-vacuo
  2. additionWater (˜50 ml) was added
  3. additionEtOAc (˜30 ml) was added
  4. customthe layers partitioned
  5. extractionthe aq layer was extracted twice more with EtOAc (˜30 ml)
  6. customthe combined organics were evaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-a625eccba95b4ed38833910576973ba5
出典データセット
uspto-grants-2012_01
特許番号
US08101775B2

反応ノート

読み込み中…