Tin tetrachloride → 2-{[1-Chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile
Reaction equation
[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]Participants
Procedure
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.
Workup
- customPurification by HPLC
Sources & evidence
- ORD record
- ord-1c1ce0e8cae74322a8c015b734b5ff5f
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06599925B2
Reaction notes
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