Chlorotrimethylsilane → HCID 13387281, compound

HRID 615582Notes

Reaction equation

HRID 615582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C([Li])CCC.Cl[Si:26]([CH3:29])([CH3:28])[CH3:27]>C(COC)OC>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[CH:11]=[C:10]([Si:26]([CH3:29])([CH3:28])[CH3:27])[O:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 13387280HCID 13387280, compoundHCID 178418339Butyllithium

Product 1

HCID 13387281HCID 13387281, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2,3-bis(4-fluorophenyl)furan (7.0 g, 27 mmoles) in 100 ml of dry dimethoxyethane was cooled to -35° and treated dropwise with n-butyl lithium (1.6M; 18.8 ml, 30 mmoles). The solution was stirred at -35° for one hour and treated with chlorotrimethylsilane (3.0 g, 27.6 mmoles). The reaction mixture was stirred at -35° for one hour and at room temperature for 24 hours. The mixture was concentrated in vacuo, suspended in 180 ml of carbon tetrachloride, and filtered through 50 g of silica gel. The filtrate was concentrated to an oil which crystallized on standing to yield 8.1 g (90%) of the title compound, m.p. 82°-83°. PMR (CDCl3) δ0.33 (s, 9H, Si(CH3)3); 6.87 (s, 1H, H--C=C--O), 6.9-7.8 (m, 8H, 2-p-FC6H4). MS: m/z 328.

Workup

  1. stirringThe reaction mixture was stirred at -35° for one hour and at room temperature for 24 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. filtrationfiltered through 50 g of silica gel
  4. concentrationThe filtrate was concentrated to an oil which
  5. customcrystallized

Sources & evidence

ORD record
ord-1f1ba2b259d54514b182fa14be4eb7f1
Source dataset
uspto-grants-1985_02
Patent number
US04500520

Reaction notes

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