Diisobutylaluminum hydride → (1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) acetaldehyde

HRID 1683987노트

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HRID 1683987 반응식
[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19](OC)=[O:20])=[C:8]2[CH3:23])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CCOCC.CCCCCC>C(Cl)Cl>[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]=[O:20])=[C:8]2[CH3:23])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 14487Diisobutylaluminum hydrideHCID 21584099Diethylether hexaneHCID 54300597HCID 54300597, 화합물

생성물 1

HCID 53659349(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) acetaldehyde수율 87.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

To a solution of ester from Step 2 (16.0 g, 39.8 mmol) in CH2Cl2 (320 mL) at -100° C. was added slowly a solution of DIBAH (1.5M/toluene, 32 mL, 47.7 mmol). The reaction was then stirred for 1-- h at -78° C., before being quenched by the addition of MeOH (3 mL), followed by 25% w/v tartaric acid (100 mL). After stirring overnight at r.t., the product was extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered, and evaporated to give a pale green syrup. This was stirred vigorously with 1:4 Et2O/hexane to give 13 g of the title compound as an off-white solid.

후처리

  1. custombefore being quenched by the addition of MeOH (3 mL)
  2. stirringAfter stirring overnight at r.t.
  3. extractionthe product was extracted with CH2Cl2
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a pale green syrup

출처 및 근거

ORD 기록
ord-813fa14c004c465eae083cb4da30d8bd
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639780

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