1,2-Dimethoxyethane → 2,2-Bis-(4-fluoro-phenyl)-4-hydroxy-butyronitrile

HRID 33606Notes

Reaction equation

HRID 33606 reaction equation
COCCOC.[BH4-].[Na+].[Li+].[Cl-].C([O:13][C:14](=O)[CH2:15][C:16]([C:31]#[N:32])([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)C>O>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)([CH2:15][CH2:14][OH:13])[C:31]#[N:32])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 433294Lithium Chloride2×HCID 4311764Sodium borohydride2×HCID 58849420HCID 58849420, compound

Product 1

HCID 184570632,2-Bis-(4-fluoro-phenyl)-4-hydroxy-butyronitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethylene glycol dimethyl ether (10 ml) was treated with sodium borohydride (142 mg) and LiCl (228 mg) and the mixture stirred for 30 min. 3-Cyano-3,3-bis-(4-fluoro-phenyl)-propionic acid ethyl ester (847 mg) was added and the mixture stirred for 6 hrs, before more sodium borohydride (36 mg) and LiCl (57 mg) were added and stirring continued overnight. The mixture was poured into water and extracted (3×) with ethyl ether. The combined organic extracts were dried over Na2SO4. Filtration, concentration and flash chromatography of the residue afforded the title compound (41%; Isolated as an oil).

Workup

  1. additionwere added
  2. stirringstirring continued overnight
  3. extractionextracted (3×) with ethyl ether
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationFiltration, concentration and flash chromatography of the residue

Sources & evidence

ORD record
ord-8ce5a370f5b44f61bb5d7d08eb6bebb6
Source dataset
uspto-grants-2008_09
Patent number
US07429618B2

Reaction notes

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