Water → HCID 178460467, compound

HRID 2392597Notes

Reaction equation

HRID 2392597 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C@H:25]3[CH2:30][CH2:29][C@H:28]([CH2:31][CH2:32][CH2:33]S(C(F)(F)F)(=O)=O)[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].[OH:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=1[OH:50])[C:45]#[N:46].[OH2:51]>COCCOC>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C@H:25]3[CH2:30][CH2:29][C@H:28]([CH2:31][CH2:32][CH2:33][O:41][C:42]4[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=4[O:50][CH2:33][CH2:32][CH2:31][C@H:28]4[CH2:27][CH2:26][C@H:25]([C:22]5[CH:21]=[CH:20][C:19]([C:16]6[CH:15]=[CH:14][C:13]([O:51][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:18][CH:17]=6)=[CH:24][CH:23]=5)[CH2:30][CH2:29]4)[C:45]#[N:46])[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 870653,4-DihydroxybenzonitrileHCID 178460473HCID 178460473, compound

Product 1

HCID 178460467HCID 178460467, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 1.50 g of 6-[4'-[trans-4-[3-(trifluoromethanesulphonyl)-propyl]-cyclohexyl]-biphenyl-4-yloxy]-hexyl acrylate and 0.155 g of 3,4-dihydroxy-benzonitrile in 25 ml of 1,2-dimethoxyethane was treated portionwise at 20° C. with 0.286 g of potassium tertiary butylate and subsequently stirred overnight at 85° C. The cooled reaction mixture was poured into 25 ml of water and then extracted three times with 20 ml of ethyl acetate. The combined organic phases were washed twice with 50 ml of water, dried over magnesium sulphate, filtered and concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which were pure according to thin-layer chromatography gave 1.10 g of 3,4-bis-[3-[trans-4-[4'-(6-acryloyloxy-hexyloxy)-biphenyl-4-yl]-cyclohexyl]-propoxy]-benzonitrile.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted three times with 20 ml of ethyl acetate
  3. washThe combined organic phases were washed twice with 50 ml of water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on silica gel
  8. customwith cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which

Sources & evidence

ORD record
ord-224914a15a434e08abe20b696e7df992
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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