Water → HCID 86753073, compound

HRID 2392601Notes

Reaction equation

HRID 2392601 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2([F:50])[C:37]([F:38])=[C:36]([C:39]3[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][CH2:48]O)=[CH:41][CH:40]=3)[CH:35]=[CH:34][CH2:33]2)=[CH:28][CH:27]=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][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2([F:50])[C:37]([F:38])=[C:36]([C:39]3[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][CH2:48][O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[CH:41][CH:40]=3)[CH:35]=[CH:34][CH2:33]2)=[CH:28][CH:27]=1)(=[O:19])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86753072HCID 86753072, compound

Product 1

HCID 86753073HCID 86753073, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3.10 g of trifluoromethanesulphonic anhydride dissolved in 10 ml of dichloromethane was added dropwise at 0° C. to a solution of 4.40 g of 4-[2',3'-difluoro-4"-(4-hydroxy-butyl)-1,2':4',1"-terphenyl-4-yloxy]-butyl acrylate and 1.18 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 4.20 g of 4-[2',3'-difluoro-4"-[4-(trifluoro-methanesulphonyloxy)-butyl]-1,2':4',1"-terphenyl-4-yloxy]-butyl 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-08d2e2b4f3cd442fb5d19b2fb93a26d7
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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