Triethylamine → NSC650613

HRID 1830115Notes

Reaction equation

[OH:1][CH2:2][C:3]([CH2:14][OH:15])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH2:12]([O:11][C:9](=[O:10])[C:3]([CH2:2][O:1][S:24]([CH3:23])(=[O:26])=[O:25])([CH2:14][O:15][S:24]([CH3:23])(=[O:26])=[O:25])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:13]

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of diethyl bis(hydroxymethyl)malonate (46.95 g, 0.21 moles) (prepared by the method of P. Block, Jr., Organic Synthesis, Collective Volume V, 381 (1973)) in methylene chloride (500 mL) was treated with triethyl amine (63 mL) and cooled to −30° C. A mixture of methylsulfonyl chloride (35 mL) in methylene chloride (40 mL) was added to the reaction mixture dropwise over 20 minutes and the reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture was then poured into ice water and the product was extracted with methylene chloride. The organic extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure and the residue was recrystallized from t-butylmethyl ether and hexane to give 2,2-bis-methylsulfonyloxymethyl-malonic acid diethyl ester (55.04 g).

Workup

additionwas added to the reaction mixture dropwise over 20 minutes
extractionthe product was extracted with methylene chloride
washThe organic extracts were washed with saturated aqueous sodium chloride
dry with materialdried over magnesium sulfate
customThe solvent was removed by rotary evaporation at reduced pressure
customthe residue was recrystallized from t-butylmethyl ether and hexane

Sources & evidence

ORD record: ord-cef72d7ef3a944678a8f2406ff4e0116
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064123B1

Reaction notes

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