Water → p-[(1,2-Difluorovinyl)dimethylsilyl]phenetole

HRID 726521Notes

Reaction equation

HRID 726521 reaction equation
[F:1][C:2]([Si:6]([CH3:17])([CH3:16])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1)=[C:3](F)[F:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1.CCOCC.Cl>[F:1][C:2]([Si:6]([CH3:16])([CH3:17])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1)=[CH:3][F:4]

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 19706492p-[(Trifluorovinyl)dimethylsilyl]phenetoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 67642293p-[(1,2-Difluorovinyl)dimethylsilyl]phenetoleYield 96.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of p-[(trifluorovinyl)dimethylsilyl]phenetole (12.0 g, 0.046 mol) in tetrahydrofuran is added dropwise to a stirred mixture of lithium aluminum hydride (1.75 g, 0.046 mol) in tetrahydrofuran at -5° C. The resultant reaction mixture is stirred at room temperature for 4 hours, cooled to 0° C., treated sequentially with ethyl acetate, water and dilute hydrochloric acid, and diluted with additional ether and dilute hydrochloric acid. The organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as a yellow liquid (10.76 g) which is identified by 1H NMR analysis as a 9:1 mixture of Z:E isomers.

Workup

  1. customThe resultant reaction mixture
  2. temperaturecooled to 0° C.
  3. customThe organic phase is separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-864c5aa6b7ea4f518009be68761dde8f
Source dataset
uspto-grants-1998_01
Patent number
US05710102

Reaction notes

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