Sodium borohydride → HCID 59516003, compound

HRID 1160425Notes

Reaction equation

HRID 1160425 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])=[C:14]([C:24]([F:27])([F:26])[F:25])[CH:13]=2)=[CH:8][C:7]=1[C:28]([F:31])([F:30])[F:29].[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])=[C:7]([C:28]([F:29])([F:30])[F:31])[CH:8]=2)=[CH:13][C:14]=1[C:24]([F:25])([F:26])[F:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 73578401HCID 73578401, compound

Product 1

HCID 59516003HCID 59516003, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,3′-Bistrifluoromethylbiphenyl-4,4′-diacrylic acid dimethyl ester (12.3 9, 26.8 mmol; prepared the same manner as 2,2′-isomer, intermediate 5, step A-B) was dissolved in 200 ml polyethylene glycol (PEG 400) and sodium borohydride (7.4 g, 196 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 and the mixture was extracted with chloroform. Chloroform extract was dried (MgSO4) and evaporated to give a residue which was submitted to chromatography on silica gel. Elution with ethyl acetate afforded 1.85 g of the title compound as white crystals.

Workup

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

Sources & evidence

ORD record
ord-4c6012046c6e4aa3a58751b3aaceb4fa
Source dataset
uspto-grants-2010_10
Patent number
US07816385B2

Reaction notes

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