Hydrochloric Acid → HCID 86639516, compound

HRID 556250Notes

Reaction equation

HRID 556250 reaction equation
[C:1]([O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17](Cl)=[O:18])[CH:11]=[CH:10]2)(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:20][CH:21]([C:29]([F:32])([F:31])[F:30])[C:22]([F:28])([F:27])[S:23]([O-:26])(=[O:25])=[O:24].[C:33]1([S+:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[F:28][C:22]([F:27])([S:23]([O-:26])(=[O:24])=[O:25])[CH:21]([O:20][C:17]([C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([O:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])[CH:8]=2)[CH:13]=1)=[O:18])[C:29]([F:30])([F:32])[F:31].[C:46]1([S+:39]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 86612198Triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropanesulfonateHCID 87227502HCID 87227502, compound

Product 1

HCID 86639516HCID 86639516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3.0 g (11 mmol) of the resulting 6-methacryloyloxynaphthalene-2-carboxylic acid chloride were added 4.9 g (10 mmol) of triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate in Synthesis Example 1-11 and 20 g of methylene chloride, which was ice cooled. To the solution, a solution of 1.1 g (11 mmol) of triethylamine and 0.2 g (2 mmol) of N,N-dimethylaminopyridine in 5 g of methylene chloride was added such that the temperature might not exceed 5° C., followed by stirring at room temperature for 3 hours. Thereafter, 11 g of 5% dilute hydrochloric acid was added. The organic layer was separated and washed with water whereupon methylene chloride was distilled off under vacuum. The residue was combined with 30 g of methyl isobutyl ketone and washed with dilute aqueous ammonia and then with water, whereupon the methyl isobutyl ketone was distilled off under vacuum. The residue was washed with diisopropyl ether and purified by silica gel chromatography. The target compound, triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(6-methacryloyloxy-naphthalene-2-carbonyloxy)-propane-1-sulfonate was obtained as colorless solid (6.5 g, yield 89%). The compound has the following structure.

Workup

  1. temperaturecooled
  2. customexceed 5° C.
  3. customThe organic layer was separated
  4. washwashed with water whereupon methylene chloride
  5. distillationwas distilled off under vacuum
  6. washwashed with dilute aqueous ammonia
  7. distillationwith water, whereupon the methyl isobutyl ketone was distilled off under vacuum
  8. washThe residue was washed with diisopropyl ether
  9. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-856a38eb15804d14b47072fcef022d0a
Source dataset
uspto-grants-2011_11
Patent number
US08057985B2

Reaction notes

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