Water → HCID 178460472, compound

HRID 2392599Notes

Reaction equation

HRID 2392599 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C@H:40]3[CH2:45][CH2:44][C@H:43]([CH2:46][CH2:47][CH2:48]O)[CH2:42][CH2:41]3)=[CH:36][CH:35]=2)=[CH:30][CH:29]=1)(=[O:19])[CH:17]=[CH2:18].N1C(C)=CC=CC=1C.O>ClCCl>[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:35]=[CH:36][C:37]([C@H:40]3[CH2:45][CH2:44][C@H:43]([CH2:46][CH2:47][CH2:48][O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH2:42][CH2:41]3)=[CH:38][CH:39]=2)=[CH:32][CH:33]=1)(=[O:19])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178460469HCID 178460469, compound

Product 1

HCID 178460472HCID 178460472, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3.47 g of trifluoromethanesulphonic anhydride dissolved in 10ml of dichloromethane were added dropwise at 0° C. to a solution of 4.77 g of 6-[4'-[trans-4-(3-hydroxy-propyl)-cyclohexyl]-biphenyl-4-yloxy]-hexyl acrylate and 1.32 g of lutidine in 100 ml of dichloromethane. The reaction mixture was stirred at 0° C. for 90 minutes and subsequently poured into 100 ml of water and extracted twice with 50 ml of dichloromethane. The combined organic phases were washed twice with 50 ml of water each time, dried over magnesium sulphate and concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) gave 5.09 g of [4'-[trans-4-[3-(trifluoromethanesulphonyloxy)-propyl]-cyclohexyl]-biphenyl-4-yloxy]-hexyl acrylate.

Workup

  1. extractionextracted twice with 50 ml of dichloromethane
  2. washThe combined organic phases were washed twice with 50 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customChromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2)

Sources & evidence

ORD record
ord-a9ae59331fd24070a454c764b3cd5192
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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