Tin tetrachloride → 2-{[1-Chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

HRID 1359235노트

반응식

HRID 1359235 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([Cl:20])=[C:15]([O:21][CH2:22][C:23]#[N:24])[CH:14]=[CH:13]2.[C:25](Cl)(=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Cl:20][C:16]1[C:17]2[C:12](=[CH:11][C:10]([C:2]3[O:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]=3[C:25](=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:15]=1[O:21][CH2:22][C:23]#[N:24]

참가 물질

5

반응물 3

HCID 24287Tin tetrachlorideHCID 61186Valeryl chlorideHCID 181828132-{[6-(1-Benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetonitrile

생성물 1

HCID 181827952-{[1-Chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Following the procedure described in Step 3 of Example 23, 2-{[6-(1-benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetonitrile (6.12 g, 18.3 mmol) was acylated with valeryl chloride (2.2 mL, 19 mmol) in presence of tin (IV) chloride (2.2 mL, 19 mmol) in methylene chloride (37 mL). Purification by HPLC using 20% ethyl acetate in hexane as the mobile phase yielded 2-{[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile as a yellow waxy solid (2.55 g), mp 86-89° C. Mass spectrum (+ESI, [M+H]+) m/z 418. 1HNMR (500 MHz, DMSO-d6): δ8.55 (d, 1H, J=1.4 Hz), 8.3 (d, 1H, J=8.9 Hz), 8.25 (d, 1H, J=9.2 Hz), 8.0-8.05 (m, 2H), 7.75-7.8 (m, 2H), 7.4-7.5 (m, 2H), 5.5 (s, 2H), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.75 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C12H20ClNO3: Calculated: C, 71.85; H, 4.82; N, 3.35. Found: C, 71.73; H, 4.59; N, 3.15.

후처리

  1. customPurification by HPLC

출처 및 근거

ORD 기록
ord-1c1ce0e8cae74322a8c015b734b5ff5f
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599925B2

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