Tin tetrachloride → Ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate

HRID 1359228Notes

Reaction equation

HRID 1359228 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][CH:22]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:14]=[CH:13]2.[C:35](Cl)(=[O:40])[CH2:36][CH2:37][CH2:38][CH3:39].[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>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:35](=[O:40])[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:15]=1[O:21][CH:22]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 24287Tin tetrachlorideHCID 61186Valeryl chlorideHCID 516892Sodium BicarbonateHCID 18182810Ethyl 2-{[6-(1-benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}-3-phenylpropanoate

Product 1

HCID 12082839Ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoateYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of ethyl 2-{[6-(1-benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}-3-phenylpropanoate (0.944 g, 2.10 mmol) in methylene chloride (4.2 mL) at −78° C. was added valeryl chloride (0.25 mL, 2.1 mmol), and tin (IV) chloride (0.25 mL, 2.1 mmol). The reaction mixture was stirred for 2 hours and 20 minutes. It was diluted with extra methylene chloride and poured into excess sodium bicarbonate solution. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The compound was purified by flash chromatography using 100% hexane and 0.5-3% ethyl acetate in hexane. It was dried at 60° C. for 30 minutes to afford ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a yellow gum (0.553 g). Mass spectrum (+ESI, [M+H]+) m/z 5351HNMR (500 MHz, DMSO-d6): δ8.35 (d, 1H, J=1.7 Hz), 8.1 (d, 1H, J=9.0 Hz), 8.05 (dd, 1H, J=7.6 Hz and 1.0 Hz), 7.9 (d, 1H, J=9.2 Hz), 7.85 (dd, 1H, J=8.9 Hz and 1.8 Hz), 7.75 (d, 1H, J=8.1 Hz), 7.25-7.45 (m, 8H), 5.3-5.35 (m, 1H), 4.1 (q, 2H, J=6.9 Hz), 3.25-3.35 (m, 2H), 2.75 (t, 2H, J=7.3 Hz), 2.5 (s, 3H), 1.5-1.6 (m, 2H), 1.05-1.2 (m, 5H), and 0.7 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C35H34O5: Calculated: C, 78.63; H, 6.41; N, 0.00. Found: C, 78.70; H, 6.30; N, 0.00.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe compound was purified by flash chromatography
  6. customIt was dried at 60° C. for 30 minutes

Sources & evidence

ORD record
ord-4e477961c660405787ce6ae906518ace
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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