Hydrochloric Acid → HCID 54402978, compound

HRID 1533483Notes

Reaction equation

HRID 1533483 reaction equation
[F:1][C:2](F)=[C:3]([F:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].C(OCC)(=O)C.Cl>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)C.O>[F:1][CH:2]=[C:3]([F:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11266029HCID 11266029, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 54402978HCID 54402978, compoundYield 97.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1,2-trifluoro-3-(4-fluoro-3-phenoxyphenyl)-1-propene (17.7 g, 0.0627 mol) in tetrahydrofuran (90 ml) is added dropwise over a period of 15 minutes to an ice cooled mixture of tetrahydrofuran (90 ml) containing 18.8 ml (0.0627 mol) of a 65 wt. % solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene. After stirring at room temperature for 20 hours, the resultant mixture is cooled, treated sequentially with ethyl acetate, water and dilute hydrochloric acid, and diluted with diethyl ether. The organic layer is separated, washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a yellow liquid (16.08 g, 97% yield). 1H NMR analysis shows this material to be a 95:5 mixture of E:Z isomers.

Workup

  1. temperaturecooled
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01230ca58b504773ad61cae59206b8cb
Source dataset
uspto-grants-2001_03
Patent number
US06207846B1

Reaction notes

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