Diisobutylaluminum hydride → 6-bromo-5-methoxy-3,4-dihydro-1H-isochromene-1-carbaldehyde

HRID 1474399ノート

反応式

HRID 1474399 の反応式
[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12](N(C)OC)=[O:13])[O:7][CH2:6][CH2:5]2.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH:12]=[O:13])[O:7][CH2:6][CH2:5]2

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 866473226-bromo-N-methyl-N,5-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide

生成物 1

HCID 772312476-bromo-5-methoxy-3,4-dihydro-1H-isochromene-1-carbaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

To a solution of 6-bromo-N-methyl-N,5-bis(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxamide (300 mg, 0.9 mmol) in 20 mL of anhydrous THF was cooled to −30° C. and then DIBAL-H (1.3 mL, 1.3 mmol, 1M) was added. The mixture was stirred at −30° C. for 2 hours. The reaction was quenched with water and extracted with DCM. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carbaldehyde was used for next step without purification.

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carbaldehyde was used for next step without purification

出典と根拠

ORDレコード
ord-b450afb7d6e149eeabee3f7502b7e991
出典データセット
uspto-grants-2015_04
特許番号
US09018211B2

反応ノート

読み込み中…