Triethylamine → 6,6-Difluoro-5-methyl-5-hexenyl methanesulfonate

HRID 917401

Reaktionsgleichung

Reaktionsgleichung von HRID 917401
C[CH:2]([OH:11])[CH2:3][CH2:4][CH2:5][C:6]([CH3:10])=[C:7]([F:9])[F:8].[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(N(CC)CC)C>O1CCCC1>[CH3:12][S:13]([O:11][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH3:10])=[C:7]([F:9])[F:8])(=[O:15])=[O:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23020199Methyl 6,6-difluoro-5-methyl-5-hexenol

Produkt 1

HCID 230203716,6-Difluoro-5-methyl-5-hexenyl methanesulfonateAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 100 ml of tetrahydrofuran, 5.00 g (33 mmol) of methyl 6,6-difluoro-5-methyl-5-hexenol and 4.20 g (37 mmol) of methanesulfonyl chloride were dissolved, followed by drop-wisely adding 4.40 g (44 mmol) of triethylamine under ice-cooling. After the end of the drop-wise addition, the reaction liquid was stirred at room temperature for 1 hour. Hydrochloric acid salt of triethylamine was filtered, followed by adding water to the filtrate and extracting with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentrating under reduced pressure to obtain 7.50 g (yield: 99%) of 6,6-difluoro-5-methyl-5-hexenyl methanesulfonate.

Aufarbeitung

  1. temperaturecooling
  2. additionAfter the end of the drop-wise addition
  3. customthe reaction liquid
  4. filtrationHydrochloric acid salt of triethylamine was filtered
  5. additionby adding water to the filtrate
  6. extractionextracting with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialby drying over anhydrous magnesium sulfate
  9. concentrationconcentrating under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-002d529bf0d3487ebd5e33d89e7c7885
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273878B2

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