Ethyl chloroformate → HCID 19096807, compound

HRID 487021Notes

Reaction equation

[C:1]1([C:9]([O-:11])=[O:10])([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3.Cl[C:45]([O:47][CH2:48][CH3:49])=[O:46]>C1COCC1>[C:4]([C:1]1([C:9]([O:11][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[O:10])[CH:2]=[CH:3]1)([O:6][CH2:7][CH3:8])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A 250 milliliter round-bottom flask was equipped with a magnetic stirrer and an addition funnel with N2 inlet. The flask was charged with 1.30 grams (0.008 mole) of monoethyl cyclopropene-1,1-dicarboxylate, 50 millilaters of dry THF, 2.3 grams (0.02 mole) of potassium carbonate (anhydrous), and 450 milligrams of dicyclohexano-18-crown-6 ether. The stirred reaction mixture was cooled to 0° C., and 0.90 gram (0.008 mole) of ethyl chloroformate in 10 millilaters of THF was added dropwise. The mixture was stirred for 21/2 hours at O° C. At this time an aliquot from the reaction mixture showed a very strong anhydride carbonyl stretch at 1820 cm-1 in the infrared indicating the formation of the mixed anhydride 1-carboethoxy-1-ethoxycarbonyloxycarbonyl-2-cyclopropene. The balance of the reaction mixture containing the mixed anhydride was carried on to Part E.

Workup

customA 250 milliliter round-bottom flask was equipped with a magnetic stirrer and an addition funnel with N2 inlet
customThe stirred reaction mixture

Sources & evidence

ORD record: ord-492b8f927a7547e7b2c0d570d504f4c7
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292937

Reaction notes

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