Hydrochloric Acid → HCID 59378478, compound

HRID 888339Notes

Reaction equation

HRID 888339 reaction equation
[CH3:1][CH:2]([CH2:6][C:7]#[CH:8])[CH2:3][CH2:4][OH:5].[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C.Cl>O1CCCC1>[CH3:9][S:10]([O:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:6][C:7]#[CH:8])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 78137849HCID 78137849, compound

Product 1

HCID 59378478HCID 59378478, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.9 g of 3-methyl-5-hexyn-1-ol and 3.0 g of methanesulfonyl chloride in 50 ml of tetrahydrofuran was added dropwise 4 ml of triethylamine at room temperature. The reaction mixture was stirred at the same temperature for 1 hour. To the reaction mixture was 10% hydrochloric acid and the extracted with ethyl acetate. The organic layer was washed sequentially with 10% hydrochloric acid and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.88 g of 3-methyl-5-hexynyl methanesulfonate.

Workup

  1. extractionthe extracted with ethyl acetate
  2. washThe organic layer was washed sequentially with 10% hydrochloric acid
  3. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f687fa237d34230b4e7fe8d4863bb7f
Source dataset
uspto-grants-2012_08
Patent number
US08247595B2

Reaction notes

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