Triethylamine → HCID 86667396, compound

HRID 2275986Notes

Reaction equation

HRID 2275986 reaction equation
[OH:1][CH:2]([CH2:9][C:10]([O:12][CH2:13][C:14]#[CH:15])=[O:11])[C:3]([O:5][CH2:6][C:7]#[CH:8])=[O:4].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(OCC)(=O)C.C(N(CC)CC)C>O>[CH3:16][S:17]([O:1][CH:2]([CH2:9][C:10]([O:12][CH2:13][C:14]#[CH:15])=[O:11])[C:3]([O:5][CH2:6][C:7]#[CH:8])=[O:4])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 13348843HCID 13348843, compound

Product 1

HCID 86667396HCID 86667396, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.10 g (0.029 mol) of the obtained di(2-propynyl) 2-hydroxysuccinate and 3.32 g (0.029 mol) of methanesulfonyl chloride were added to 40 g of ethyl acetate, and 2.93 g (0.029 mol) of triethylamine was dropwise added thereto within a range of from 5° C. to 15° C., taking 15 minutes. This was reacted at room temperature for 1 hour, the disappearance of the starting materials was confirmed through gas chromatography, and 20 ml of water was added for liquid-liquid separation. The organic layer was concentrated under reduced pressure. The residue was purified through column chromatography (Wakogel C-200, elution with hexane/ethyl acetate=2/1) to give 4.50 g (yield 54%) of the intended di(2-propynyl) 2-(methanesulfonyloxy)succinate.

Workup

  1. additionwas dropwise added
  2. customThis was reacted at room temperature for 1 hour
  3. additionwas added for liquid-liquid separation
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified through column chromatography (Wakogel C-200, elution with hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-a266a27b2a7149159f17ccfc62bb0564
Source dataset
uspto-grants-2015_09
Patent number
US09130244B2

Reaction notes

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