Hydrochloric Acid → HCID 11515081, compound

HRID 491252Notes

Reaction equation

HRID 491252 reaction equation
C([Li])CCC.[F:6][C:7]([F:15])([F:14])[CH:8]([OH:13])[C:9]([F:12])(F)[F:10].[C:16]([O:21][CH2:22][C:23](=[O:25])[CH3:24])(=[O:20])[C:17]([CH3:19])=[CH2:18].Cl.[O:27]1CCCC1>CCCCCC>[C:16]([O:21][CH2:22][C:23]([CH3:24])([OH:25])[C:9]([F:12])([F:10])[C:8]([OH:27])([OH:13])[C:7]([F:15])([F:14])[F:6])(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 11804856HCID 11804856, compoundHCID 178418339Butyllithium

Product 1

HCID 11515081HCID 11515081, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

In a nitrogen atmosphere at 5° C., 1290 ml of 1.6M butyllithium in hexane was added to a mixture of 168 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 1200 g of tetrahydrofuran, followed by one hour of stirring at 5° C. Then 142 g of 2-oxopropyl methacrylate was added at 5° C. The mixture was stirred for 10 hours, after which dilute hydrochloric acid was added to quench the reaction and neutralize the reaction mixture. This was followed by conventional aqueous work-up and purification by silica gel column chromatography, collecting 253 g of the product (yield 82%).

Workup

  1. stirringThe mixture was stirred for 10 hours
  2. customto quench
  3. customthe reaction
  4. customThis was followed by conventional aqueous work-up and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-f9e503e4958a464ba81f6a31b5b4b7a2
Source dataset
uspto-grants-2009_05
Patent number
US07531289B2

Reaction notes

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