Triethylamine → HCID 53709047, compound

HRID 2165354Notes

Reaction equation

HRID 2165354 reaction equation
[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][CH:4]([OH:11])[C:5]([CH3:10])([CH3:9])[C:6](=[O:8])[CH3:7].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[Cl:1][C:2]([C:12]([F:13])([F:14])[F:15])=[CH:3][CH:4]([O:11][S:24]([CH3:23])(=[O:26])=[O:25])[C:5]([CH3:9])([CH3:10])[C:6](=[O:8])[CH3:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54469267HCID 54469267, compound

Product 1

HCID 53709047HCID 53709047, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

733 g (3 mol) of 6-chloro-3,3-dimethyl-4-hydroxy-7,7,7-trifluoro-hept-5-en-2-one, 360 g (3.6 mol) of triethylamine and 1.5 g of 4-(N,N-dimethylamino)pyridine in 1 l of toluene were admixed at 5° C. with 378 g (3.6 mol) of methanesulfonyl chloride. The mixture was subsequently stirred at 25° C. for 3 hours, the precipitate was filtered off, and the filtrate was extracted with dilute hydrochloric acid and with saturated sodium bicarbonate solution. Drying and concentrating the organic phase gave 948 g of product. Melting point: 50°-52° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. extractionthe filtrate was extracted with dilute hydrochloric acid and with saturated sodium bicarbonate solution
  3. customDrying
  4. concentrationconcentrating the organic phase

Sources & evidence

ORD record
ord-2b941ee8c89d4b8baf050300d28b235f
Source dataset
uspto-grants-1990_07
Patent number
US04939303

Reaction notes

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