Sodium Hydroxide → 7-Methyl-2,3-dihydro-1H-indole

HRID 1275647

반응식

HRID 1275647 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 702757-MethylindoleHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 123777887-Methyl-2,3-dihydro-1H-indole수율 111.5%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a stirred solution of 7-methylindole (10.27 g, 78.3 mmol) in glacial acetic acid (50 mL) is added sodium cyanoborohydride (6.33 g, 100.7 mmol) portionwise over a 5 minute period. The reaction solution is allowed to stir for 1 hour. The solution is diluted with water (500 mL) and basified with 50% sodium hydroxide solution. The basic solution is extracted with three 250 mL portions of diethyl ether. The organic fractions are combined, dried over anhydrous potassium carbonate, filtered and evaporated to give a pink oil. The oil is purified by silica gel column chromatography using 20% ethyl acetate/hexanes as eluent to give 11.63 g of 2,3-dihydro-7-methylindole as a colorless oil (94% yield).

후처리

  1. extractionThe basic solution is extracted with three 250 mL portions of diethyl ether
  2. dry with materialdried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a pink oil
  6. customThe oil is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6311792080f14d9093bb90b63962aede
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162818

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