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

HRID 1683987ノート

反応式

HRID 1683987 の反応式
[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

参加物

5

反応物 3

HCID 14487Diisobutylaluminum hydrideHCID 21584099Diethylether hexaneHCID 54300597HCID 54300597、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-813fa14c004c465eae083cb4da30d8bd
出典データセット
uspto-grants-1997_06
特許番号
US05639780

反応ノート

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