Sodium borohydride → HCID 59516006, compound

HRID 1160424Notes

Reaction equation

HRID 1160424 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20](OC)=[O:21])=[CH:14][C:13]=2[C:24]([F:27])([F:26])[F:25])=[C:8]([C:28]([F:31])([F:30])[F:29])[CH:7]=1.[BH4-].[Na+]>O>[OH:21][CH2:20][CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][OH:2])=[CH:7][C:8]=2[C:28]([F:29])([F:30])[F:31])=[C:13]([C:24]([F:25])([F:26])[F:27])[CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 73578400HCID 73578400, compound

Product 1

HCID 59516006HCID 59516006, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2′-Bistrifluoromethylbiphenyl-4,4′-diacrylic acid dimethyl ester (11.5 g, 25.1 mmol) was dissolved in 200 ml polyethylene glycol (PEG 400) and sodium borohydride (6.5 g, 172 mmol) was added gradually during 30 min at 130° C. The mixture was heated at this temperature for 6 h. After cooling water was added, the mixture was extracted with chloroform, dried (MgSO4) and evaporated to give a residue which was submitted to chromatography on silica gel. Elution with ethyl acetate afforded 3.57 g (35%) of the title compound as an oil.

Workup

  1. temperatureThe mixture was heated at this temperature for 6 h
  2. additionwas added
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a residue which
  7. washElution with ethyl acetate

Sources & evidence

ORD record
ord-aa7acb0d28ce43be99e93fa51da04dc7
Source dataset
uspto-grants-2010_10
Patent number
US07816385B2

Reaction notes

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