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

HRID 1359225Notes

Reaction equation

HRID 1359225 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]([CH3:20])=[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>[CH3:20][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

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 61186Valeryl chlorideHCID 181827852-{[6-(1-Benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}acetonitrile

Product 1

HCID 181828012-{[1-Methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrileYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure described in Step 2 of Example 1, 2-{[6-(1-benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}acetonitrile (1.15 g, 3.67 mmol) was acylated with valeryl chloride (0.52 mL, 4.4 mmol), in presence of tin (IV) chloride (0.52 mL, 4.4 mmol) in methylene chloride (15 mL). 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile was prepared. Purification by flash chromatography (Biotage apparatus) using 10-20% chloroform in hexane and 100% hexane and 0.5-5% ethyl acetate in hexane as eluants yielded the title compound as a yellow gum (0.458 g). 1HNMR (300 MHz, DMSO-d6): δ8.45 (s, 1H), 8.2 (d, 1H, J=7.7 Hz), 8.05 (t, 2H, J=8.8 Hz), 7.95 (d, 1H, J=7.7 Hz), 7.75 (d, 1H, J=7.7 Hz), 8.65 (d, 1H, J=7.7 Hz), 7.4-7.5 (m, 2H), 5.35 (s, 2H), 2.75 (t, 2H, J=8.1 Hz), 2.55 (s, 3H), 1.5-1.6 (m, 2H), 1.1-1.25 (m, 2H), and 0.7 ppm (t, 3H, J=8.8 Hz).

Workup

  1. custom2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile was prepared
  2. customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-7a505c6233a948d195e9ae4b4822fc0e
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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