Tin tetrachloride → 1-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

HRID 1359207노트

반응식

HRID 1359207 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=1)[CH:7]=[CH:6]2.[C:22](Cl)(=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[C:17]=1[C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH:7]=[CH:6]2

참가 물질

5

반응물 3

HCID 24287Tin tetrachlorideHCID 66054Isovaleryl chlorideHCID 110766242-(6-Methoxy-2-naphthyl)-1-benzofuran

생성물 1

HCID 181827841-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

Following the procedure described in Step 2 of Example 1, 2-(6-methoxy-2-naphthyl)-1-benzofuran (3.00 g, 10.9 mmol), was acylated with isovaleryl chloride (1.9 mL, 16 mmol), in presence of tin (IV) chloride (1.7 mL, 14 mmol) in chloroform (60 mL). Purification by flash chromatography using 15-100% chloroform in hexane as an eluant then by using the Biotage apparatus using 1.5% ethyl acetate in hexane as an eluant yielded the title compound as a yellow wax (1.34 g); 1HNMR (200 MHz, DMSO-d6): δ8.35 (s, 1H), 8.0 (d, 3H, J=8.2 Hz), 7.8 (d, 1H, J=10.2 Hz), 7.7 (d, 1H, J=7.7 Hz), 7.35-7.55 (m, 3H), 7.3 (d, 1H, J=8.7 Hz), 3.95 (s, 3H), 2.6 (d, 2H, J=7.7 Hz), 2.0-2.1 (m, 1H), and 0.75 ppm (d, 6H, J=7.7 Hz).

후처리

  1. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-142eea6ab14b40a787bbe2db0bd48c25
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599925B2

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