Tetrahydrofuran → HCID 14738110, compound

HRID 1472233Notes

Reaction equation

HRID 1472233 reaction equation
O1CCCC1.[CH3:6][C:7]([CH3:13])([CH:11]=[CH2:12])[CH2:8][CH2:9][OH:10].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>O>[CH3:6][C:7]([CH3:13])([CH:11]=[CH2:12])[CH2:8][CH2:9][O:10][S:22]([CH3:21])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1257909853589-56-3

Product 1

HCID 14738110HCID 14738110, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a tetrahydrofuran (30 ml) solution of 3,3-dimethyl-4-penten-1-ol (3.6 g), triethylamine (4.1 g) and methanesulfonyl chloride (4.3 g) were added at 0° C., followed by raising the temperature to room temperature and further stirring for 30 minutes. Water was added thereto and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to obtain a crude product (5.7 g) of methanesulfonic acid 3,3-dimethyl-4-pentenyl ester. This crude product was subjected to a subsequent reaction without being purified.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-117e12157de34d1da4edde71378d2972
Source dataset
uspto-grants-2015_04
Patent number
US09012493B2

Reaction notes

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