Chlorotrimethylsilane → Silane, [[1-(4-fluorophenyl)ethenyl]oxy]trimethyl-

HRID 275485Notes

Reaction equation

HRID 275485 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)=[O:3].C(N(CC)CC)C.Cl[Si:19]([CH3:22])([CH3:21])[CH3:20].[Na]>C(#N)C>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([O:3][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH2:1])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 98284'-FluoroacetophenoneHCID 5360545Sodium

Product 1

HCID 10398215Silane, [[1-(4-fluorophenyl)ethenyl]oxy]trimethyl-Yield 100.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 17.7 g (128 mmol) of 4-fluoroacetophenone (Aldrich) and 20.7 mL (192 mmol) of triethylamine at ambient temperature was treated with 24.4 mL (192.3 mmol) of chlorotrimethylsilane and allowed to stir of 20 minutes prior to the slow addition of a suspension of 30 g (200 mmol) of sodium iodode in 200 mL of acetonitrile. The extracts were combined, dried (K2CO3), and concentrated in vacuo to give 27 g of crude 1-fluoro-4-[1[(trimethylsilyl)oxy]ethenyl]benzene as an oil: NMR (CDCl3) δ 0.28 (s, 9H), 4.41 (d, J=2 Hz, 1H), 4.84 (d, J=2 Hz, 1H), 7.00 (d, J=8 Hz, 2H), 7.53 -7.60 (m, 2H).

Workup

  1. dry with materialdried (K2CO3)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-816c174d5af942aaa6dcb39d88951a2d
Source dataset
uspto-grants-1995_02
Patent number
US05393790

Reaction notes

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