Water → HCID 178460469, compound

HRID 2392598Notes

Reaction equation

HRID 2392598 reaction equation
[BH4-].[Na+].O.[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C@H:28]3[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH:36]=[O:37])[CH2:30][CH2:29]3)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)(=[O:7])[CH:5]=[CH2:6]>O1CCOCC1>[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:23]=[CH:24][C:25]([C@H:28]3[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH2:36][OH:37])[CH2:30][CH2:29]3)=[CH:26][CH:27]=2)=[CH:20][CH:21]=1)(=[O:7])[CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 962Water2×HCID 4311764Sodium borohydrideHCID 178460468HCID 178460468, compound

Product 1

HCID 178460469HCID 178460469, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.123 g of sodium borohydride and 10 ml of water was treated dropwise at 20° C. with a solution of 5.00 g of 6-[4'-[trans-4-(3-oxo-propyl)-cyclohexyl]-biphenyl-4-yloxy]-hexyl 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 4.77 g of 6-[4'-[trans-4-(3-hydroxy-propyl)-cyclohexyl]-biphenyl-4-yloxy]-hexyl 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-5b5fd2b818154b9ca702250127ab1815
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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