Water → HCID 86678767, compound

HRID 1620594Notes

Reaction equation

HRID 1620594 reaction equation
[CH3:1][C:2]([OH:8])([CH3:7])[C:3]#[C:4][CH2:5][OH:6].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].O>C1COCC1>[CH3:16][S:17]([O:6][CH2:5][C:4]#[C:3][C:2]([OH:8])([CH3:7])[CH3:1])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 827664-Methylpent-2-yne-1,4-diol

Product 1

HCID 86678767HCID 86678767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methylpent-2-yne-1,4-diol (Synthesis 2001. 1013.) (1.00 g) in THF (40 mL) were added triethylamine (1.85 mL) and methanesulfonyl chloride (0.69 mL). The reaction mixture was stirred at room temperature overnight under a nitrogen atmosphere, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.57 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8b073f0c07e84f2d9b559d0dc971a751
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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