Ethyl Acetate → HCID 86756551, compound

HRID 1532950Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:5][P:6]([CH2:11][P:12]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13])([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].[C:20]([C:26]([O:28][CH3:29])=[O:27])#[C:21][C:22]([O:24][CH3:25])=[O:23].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:25][O:24][C:22](=[O:23])/[C:21](/[CH:11]([P:6]([O:8][CH2:9][CH3:10])([O:5][CH2:3][CH3:4])=[O:7])[P:12]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13])=[CH:20]\[C:26]([O:28][CH3:29])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

In a suspension of 1.33 g of sodium hydride (60% in oil) in 120 ml of toluene are added dropwise 10 g of bis(diethoxyphosphoryl)methane dissolved in 20 ml of toluene. The reaction mixture is kept at room temperature under stirring for 1 hour, then it is cooled to 0° C. and added dropwise with a solution of dimethyl acetylenedicarboxylate (5.17 g) in 20 ml of toluene. After 1 hour under stirring the reaction mixture is added with ethyl acetate until dissolution of the formed gummy solid occurs and it is washed firstly with 1 N hydrochloric acid (30 ml) then with water (2×30 ml). The organic phase is dried over sodium sulfate and the solvent is evaporated under reduced pressure, to give a residue (12.9 g) which, after purification by silica gel chromatography (300 g; eluent:petroleum ether/isopropanol 7:3) furnishes 9.6 g of pure product.

Workup

customis kept at room temperature
stirringAfter 1 hour under stirring the reaction mixture
washit is washed firstly with 1 N hydrochloric acid (30 ml)
dry with materialThe organic phase is dried over sodium sulfate
customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record: ord-39384b14032748e6b8871713a6804618
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06207655B1

Reaction notes

Loading…