Water → HCID 86753072, compound

HRID 2392600Notes

Reaction equation

HRID 2392600 reaction equation
[BH4-].[Na+].O.[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([F:38])[C:25]([F:26])=[C:24]([C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][CH:36]=[O:37])=[CH:29][CH:28]=3)[CH:23]=[CH:22][CH2:21]2)=[CH:16][CH:15]=1)(=[O:7])[CH:5]=[CH2:6]>O1CCOCC1>[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([F:38])[C:25]([F:26])=[C:24]([C:27]3[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][CH2:35][CH2:36][OH:37])=[CH:31][CH:32]=3)[CH:23]=[CH:22][CH2:21]2)=[CH:16][CH:15]=1)(=[O:7])[CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 962Water2×HCID 4311764Sodium borohydrideHCID 86753071HCID 86753071, compound

Product 1

HCID 86753072HCID 86753072, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.119 g of sodium borohydride and 10 ml of water was treated dropwise at 0° C. with a solution of 5.00 g of 4-[2',3'-difluoro-4"-(4-oxo-butyl)-1,2':4',1"-terphenyl-4-yloxy]-butyl acrylate in 50 ml of dioxan. The mixture was subsequently stirred at room temperature for 1 hour. The reaction mixture was poured into 50 ml of water, the phases were separated and the aqueous phase was extracted twice with 25 ml of ethyl acetate each time. The combined organic phases were washed twice with 50 ml of water each time, dried over magnesium sulphate, filtered and concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) gave 4.49 g of 4-[2',3'-difluoro-4"-(4-hydroxy-butyl)-1,2':4',1"-terphenyl -4-yloxy]-butyl acrylate.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with 25 ml of ethyl acetate each time
  3. washThe combined organic phases were washed twice with 50 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2)

Sources & evidence

ORD record
ord-74ca211920a7449eaee3f9cf5db60bc9
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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