Hydrochloric Acid → HCID 23149408, compound

HRID 1788348Notes

Reaction equation

HRID 1788348 reaction equation
[F:1][C:2]([F:21])([S:17]([O-:20])(=[O:19])=[O:18])[CH:3]([O:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([F:7])([F:6])[F:5].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([S+:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:24]=1.[C:42](Cl)(=[O:46])[C:43]([CH3:45])=[CH2:44].C(N(CC)CC)C.Cl>ClCCl>[F:21][C:2]([F:1])([S:17]([O-:20])(=[O:18])=[O:19])[CH:3]([O:8][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([F:5])([F:7])[F:6].[C:42]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S+:29]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)(=[O:46])[C:43]([CH3:45])=[CH2:44]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 23149398HCID 23149398, compound

Product 1

HCID 23149408HCID 23149408, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 15 g of dichloromethane was dissolved 3 g of (4-hydroxyphenyl)diphenylsulfonium 1,1,3,3,3-pentafluoro-2-benzoyloxypropane-1-sulfonate (PAG29) prepared in Synthesis Example 45. Methacryloyl chloride, 1 g, was added to the solution, which was cooled in an ice bath, and 0.9 ml of triethylamine was added dropwise. 30 g of 3N dilute hydrochloric acid was added, after which the organic layer was separated, washed with 30 g of water three times, and concentrated. The concentrate was purified by silica gel column chromatography (elute: dichloromethane/methanol 20/1 in weight ratio), after which diethyl ether was added to the concentrate for crystallization. The crystals were filtered and dried, obtaining the target compound in an amount of 3.5 g.

Workup

  1. customprepared in Synthesis Example 45
  2. temperaturewas cooled in an ice bath
  3. customafter which the organic layer was separated
  4. washwashed with 30 g of water three times
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (elute: dichloromethane/methanol 20/1 in weight ratio)
  7. additionafter which diethyl ether was added to the
  8. concentrationconcentrate for crystallization
  9. filtrationThe crystals were filtered
  10. customdried
  11. customobtaining the target compound in an amount of 3.5 g

Sources & evidence

ORD record
ord-9655de8e3c684ad7ac0f71f73a5f3dc5
Source dataset
uspto-grants-2009_03
Patent number
US07511169B2

Reaction notes

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