Triethylamine → HCID 86656003, compound

HRID 389835Notes

Reaction equation

HRID 389835 reaction equation
C(N(CC)CC)C.[CH:8]([O:10][CH2:11][C:12]#[C:13][CH2:14][OH:15])=[O:9].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(=O)(O)[O-].[Na+]>C(=O)(OC)OC>[CH3:16][S:17]([O:15][CH2:14][C:13]#[C:12][CH2:11][O:10][CH:8]=[O:9])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86656004HCID 86656004, compound

Product 1

HCID 86656003HCID 86656003, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 12021Dimethyl CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

41.5 g (0.409 mol) of triethylamine was added to 300 ml of dimethyl carbonate solution of 44.0 g (0.386 mol) of 4-formyloxy-2-butyn-1-ol, and cooled to 0° C. 46.9 g (0.409 mol) of methanesulfonyl chloride was dropwise added to the solution while the inner temperature was controlled to be not higher than 15° C. After the addition, this was stirred at 25° C. for 1.5 hours, the reaction mixture was poured into an aqueous saturated sodium bicarbonate solution, the aqueous layer was separated, and the organic layer was concentrated to give 72.6 g (yield 98%) 4-formyloxy-2-butyn-1-yl methanesulfonate. For use in the battery test, this was purified through silica gel column chromatography.

Workup

  1. customto be not higher than 15° C
  2. additionAfter the addition
  3. customthe aqueous layer was separated
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-cace5d0197254a189049ee2bdbac4450
Source dataset
uspto-grants-2013_02
Patent number
US08383274B2

Reaction notes

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