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

HRID 1187142노트

반응식

HRID 1187142 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-30 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cff9f47ef1394269914c5e7677025c15
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673920B2

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