Triethylamine → 4,4-Difluoro-3-Methyl-3-Buten-1-Yl Methanesulfonate

HRID 917399Notes

Reaction equation

HRID 917399 reaction equation
[F:1][C:2]([F:8])=[C:3]([CH3:7])[CH2:4][CH2:5][OH:6].[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C>O1CCCC1>[CH3:9][S:10]([O:6][CH2:5][CH2:4][C:3]([CH3:7])=[C:2]([F:8])[F:1])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15191149HCID 15191149, compound

Product 1

HCID 230202374,4-Difluoro-3-Methyl-3-Buten-1-Yl MethanesulfonateYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 100 ml of tetrahydrofuran, 4.45 g (36 mmol) of 4,4-difluoro-3-methyl-3-butenol and 4.59 g (40 mmol) of methanesulfonyl chloride were dissolved, followed by drop-wisely adding 4.42 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 7.20 g (yield: 99%) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate.

Workup

  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

Sources & evidence

ORD record
ord-e680c7682ab7466aa6d496a144f3bdf2
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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