Tributylstannane → 1-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid methyl ester

HRID 1964206Notes

Reaction equation

HRID 1964206 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[C:12](I)[C:11]([O:15][CH2:16][C:17]([CH3:19])=[CH2:18])=[C:10](I)[CH:9]=2)[CH2:7][CH2:6]1)=[O:4].CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]3[O:15][CH2:16][C:17]([CH3:19])([CH3:18])[C:10]=3[CH:9]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 591292181-[3,5-Diiodo-4-(2-methyl-allyloxy)-phenyl]cyclopropane-carboxylic acid methyl ester

Product 1

HCID 591293551-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid methyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-[3,5-diiodo-4-(2-methyl-allyloxy)-phenyl]-cyclopropane-carboxylic acid methyl ester (3.5 g, 7.0 mmol) in toluene (15 mL) was added Bu3SnH (2.4 g, 8.4 mmol) and AIBN (0.1 g, 0.7 mmol). The mixture was heated at reflux overnight. The reaction mixture was concentrated under vacuum and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1) to give 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid methyl ester (1.05 g, 62%). 1H NMR (400 MHz, CDCl3) δ 7.10-7.07 (m, 2 H), 6.71 (d, J=8 Hz, 1 H), 4.23 (s, 2 H), 3.62 (s, 3 H), 1.58-1.54 (m, 2 H), 1.34 (s, 6 H), 1.17-1.12 (m, 2 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-7d159e7f647f4e2b8809f6d5b2ec2d11
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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