Acetic Acid → 1-[3-(1,3-Dioxolan-2-yl)benzyl]-7-cyanomethoxyindole

HRID 1198551

반응식

HRID 1198551 반응식
[H-].[Na+].[C:3]([CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2)#[N:4].[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br.C(O)(=O)C>O1CCCC1.ClCCl>[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][CH2:5][C:3]#[N:4])[CH:12]=[CH:13]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 150540207-(Cyanomethoxy)indoleHCID 191025633-(1,3-Dioxolan-2-yl)benzyl bromide

생성물 1

HCID 191026031-[3-(1,3-Dioxolan-2-yl)benzyl]-7-cyanomethoxyindole

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

60% Sodium hydride dispersion in mineral oil (90 mg, 2.25 mmol) was added to a stirred, cooled solution of 7-cyanomethoxyindole (Example 1a) (0.32 g., 1.86 mmol) in tetrahydrofuran (8 ml). The dark mixture was stirred for 15 minutes at room temperature then cooled again whilst a solution of 3-(1,3-dioxolan-2-yl)benzyl bromide (0.50 g., 2.06 mmol) in tetrahydrofuran (2 ml) was added. The mixture was stirred at room temperature for 20 hours then treated with glacial acetic acid (130 μl), diluted with dichloromethane, washed with water, dried and evaporated. The residue was chromatographed on silica in ethyl acetate-hexane (1:3).

후처리

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 20 hours
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica in ethyl acetate-hexane (1:3)

출처 및 근거

ORD 기록
ord-482a656edc4e4126845732fd2c629cc9
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281593

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