Tin tetrachloride → 2-Cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanone

HRID 1359211Notes

Reaction equation

HRID 1359211 reaction equation
[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.[CH:22]1([CH2:27][C:28](Cl)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23]1.[Sn](Cl)(Cl)(Cl)Cl>C(=S)=S>[CH:22]1([CH2:27][C:28]([C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14][C:13]=2[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 3485182Cyclopentylacetyl chlorideHCID 110766242-(6-Methoxy-2-naphthyl)-1-benzofuran

Product 1

HCID 181828082-Cyclopentyl-1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-ethanoneYield 59.1%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Following the procedure described in Step 2 of Example 1, 2-(6-methoxy-2-naphthyl)-1-benzofuran (6.00 g, 21.9 mmol) was acylated with 2-cyclopentylacetyl chloride (3.51 g, 23.9 mmol) using tin (IV) chloride (2.8 mL, 24 mmol) in carbon disulfide (120 mL). Purification by flash chromatography (Biotage apparatus) using 10-25% chloroform in hexane and 0.5-1% ethyl acetate in hexane as eluants furnished the title compound as a yellow gum (4.98 g); 1HNMR (200 MHz, DMSO-d6): δ8.35 (s, 1H), 8.0 (d, 3H, J=8.7 Hz), 7.8 (d, 1H, J=8.7 Hz), 7.7-7.8 (m, 1H), 7.35-7.5 (m, 3H), 7.2-7.35 (m, 1H), 3.95 (s, 3H), 2.75 (d, 2H, J=7.7 Hz), 2.1-2.3 (m, 1H), 1.5-1.75 (m, 2H), 1.3-1.5 (m, 4H), and 0.8-1.1 ppm (m, 2H).

Workup

  1. customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-3df471e8339640c99363fbaa223847ab
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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