Boron tribromide → 8-Hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

HRID 1184494ノート

反応式

HRID 1184494 の反応式
C[O:2][C:3]1[C:8]2[O:9][CH:10]([CH3:14])[C:11](=[O:13])[NH:12][C:7]=2[CH:6]=[C:5]([CH:15]=[O:16])[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:8]2[O:9][CH:10]([CH3:14])[C:11](=[O:13])[NH:12][C:7]=2[CH:6]=[C:5]([CH:15]=[O:16])[CH:4]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 821540558-Methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

生成物 1

HCID 866642258-Hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde収率 96.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

In a 20 mL scintillation vial was added 8-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde 17 (111 mg, 0.502 mmol) and boron tribromide (2.0 mL, 2.000 mmol) in DCM (2.5 mL) and stirred at −10° C. for 1 h then slowly warmed to 23° C. and stirred overnight. The reaction was quenched with MeOH, taken up in EtOAc, washed with water and brine, dried over MgSO4, and concentrated in vacuo to give the title compound as a tan solid (100 mg, 0.483 mmol, 96% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (d, J=6.82 Hz, 3H) 4.75 (q, J=6.82 Hz, 1H) 6.92 (d, J=2.02 Hz, 1H) 7.03 (d, J=1.77 Hz, 1H) 9.74 (s, 1H) 9.98 (br. s., 1H) 10.85 (s, 1H). ESI-MS: m/z 208.0 (M+H)+.

後処理

  1. temperaturethen slowly warmed to 23° C.
  2. stirringstirred overnight
  3. customThe reaction was quenched with MeOH
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d6f2f54dc41847c3ac56b79d8073b881
出典データセット
uspto-grants-2014_03
特許番号
US08669249B2

反応ノート

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