Triethylamine → HCID 86678449, compound

HRID 592496Notes

Reaction equation

HRID 592496 reaction equation
[CH3:1][CH:2]([OH:7])[CH:3]([OH:6])[CH2:4][CH3:5].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:7][CH:2]([CH:3]([O:6][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:4][CH3:5])[CH3:1])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 123505Pentane-2,3-diol

Product 1

HCID 86678449HCID 86678449, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Pentane-2,3-diol 1.04 g (10.0 mole) and triethylamine 2.23 g (22.0 mole) were dissolved in 40 mL of methylene chloride, and methanesulfonyl chloride 2.52 g (22.0 mole) was dropwise added thereto in a range of 0 to 5° C. and stirred at 0° C. for 30 minutes. After the raw materials were confirmed to be exhausted by gas chromatography analysis, the organic layer was washed with 20 ml of water and then 20 ml of a saturated salt solution. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was refined by column chromatography (Wako Gel C-200, hexane/ethyl acetate=2/1 eluted) to obtain 2.24 g of pentane-2,3-diyl dimethanesulfonate (pale orange liquid; novel compound) which was the targeted product (yield: 86%).

Workup

  1. washthe organic layer was washed with 20 ml of water
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was refined by column chromatography (Wako Gel C-200, hexane/ethyl acetate=2/1 eluted)

Sources & evidence

ORD record
ord-f8b606a2b7504d0a91eaefe84a6858d5
Source dataset
uspto-grants-2016_01
Patent number
US09240614B2

Reaction notes

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