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

HRID 1359206Notes

Reaction equation

HRID 1359206 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.[C:22]([CH2:26][C:27](Cl)=[O:28])([CH3:25])([CH3:24])[CH3:23].[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:27](=[O:28])[CH2:26][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 815143,3-Dimethylbutanoyl chlorideHCID 110766242-(6-Methoxy-2-naphthyl)-1-benzofuran

Product 1

HCID 181828041-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-3,3-dimethyl-1-butanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the procedure described in Step 2 of Example 1, the title compound was prepared from 2-(6-methoxy-2-naphthyl)-1-benzofuran (3.00 g, 10.9 mmol), t-butyl acetyl chloride (2.3 mL, 16 mmol), and tin (IV) chloride (1.7 mL, 14 mmol) in chloroform (60 mL). The reaction mixture was refluxed for 24 hours. Purification by HPLC using 7-8% ethyl acetate in hexane as the mobile phase yielded a yellow solid (1.09 g), mp ˜140° C. 1HNMR (200 MHz, DMSO-d6): δ8.35 (s, 1H), 7.9-8.1 (m, 3H), 7.7-7.85 (m, 2H), 7.35-7.5 (m, 3H), 7.3 (d, 1H, J=9.0 Hz), 3.95 (s, 3H), 2.75 (s, 2H), and 0.85 ppm (s, 9H).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. customPurification by HPLC

Sources & evidence

ORD record
ord-308b59313c4c41e49705b2210741f33e
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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