Magnesium diiodide → (1RS,2SR,6RS,7RS)-4-(2,4,6-trimethylphenyl)-8-trimethylsilylethynyl-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

HRID 407847Notes

Reaction equation

HRID 407847 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[CH:11]=[CH:10][O:9][CH:8]=1)([CH3:4])[CH3:3].[I-].[Mg+2].[I-].[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[CH:24]1[C:28](=[O:29])[CH:27]=[CH:26][C:25]1=[O:30]>>[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[CH:24]1[C:25](=[O:30])[CH:26]2[CH:27]([CH:10]3[O:9][CH:8]2[CH:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[CH2:11]3)[C:28]1=[O:29]

Participants

4

Reactant 3

HCID 5462737Magnesium diiodideHCID 16217672[2-(Furan-3-yl)ethynyl]trimethylsilaneHCID 666844242-(2,4,6-Trimethylphenyl)cyclopent-4-ene-1,3-dione

Product 1

HCID 67283755(1RS,2SR,6RS,7RS)-4-(2,4,6-trimethylphenyl)-8-trimethylsilylethynyl-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

Procedure

3-(Trimethylsilylethynyl)furan (10.0 g, 61 mmol) and magnesium iodide (1.11 g, 4 mmol) are added to 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (4.34 g, 20 mmol) and the mixture is stirred at room temperature for 3 days. The reaction mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7RS)-4-(2,4,6-trimethylphenyl)-8-trimethylsilylethynyl-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b31ccfc02a9540188627111323e0e3a6
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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