Ethyl chloroformate → HCID 72985482, compound

HRID 900514Notes

Reaction equation

HRID 900514 reaction equation
C([Cl:6])(=O)OCC.[CH2:7]([O:9][CH:10](OCC)[CH:11]1[CH2:15][CH2:14][O:13][CH:12]1OCC)[CH3:8]>>[Cl:6][CH2:14][CH2:15][C:11](=[CH:10][O:9][CH2:7][CH3:8])[CH:12]=[O:13]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 115794243-(diethoxymethyl)-2-ethoxytetrahydrofuran

Product 1

HCID 72985482HCID 72985482, compoundYield 95.8%

Procedure

3-(Diethoxymethyl)-2-ethoxytetrahydrofuran (20.03 g, 91.8 mmol) obtained by the method of Reference Example 1, toluene (46.0 g) and pyridine (0.22 g, 2.8 mmol) were added to a 100 ml three-necked flask equipped with a thermometer, a stirrer and a dimroth condenser, and the mixture was heated to 100° C. to 106° C. under a nitrogen atmosphere. Ethyl chlorocarbonate (19.92 g, 183.5 mmol, 2-fold mol relative to 3-(diethoxymethyl)-2-ethoxytetrahydrofuran) was added dropwise to the mixture over 1 hr. After completion of the dropwise addition, the mixture was reacted at the same temperature for 6 hr, and the reaction solution was analyzed by gas chromatography. As a result, the conversion ratio of 3-(diethoxymethyl)-2-ethoxytetrahydrofuran was 100%, and 4-chloro-2-ethoxymethylidenebutanal (14.3 g, 87.9 mmol, yield 95.8%) was produced.

Workup

  1. additionwere added to a 100 ml three-necked flask
  2. customequipped with a thermometer, a stirrer and a dimroth condenser
  3. temperaturethe mixture was heated to 100° C. to 106° C. under a nitrogen atmosphere
  4. additionAfter completion of the dropwise addition
  5. customthe mixture was reacted at the same temperature for 6 hr

Sources & evidence

ORD record
ord-4839a98532a24e8fa605210ec5695d24
Source dataset
uspto-grants-2008_04
Patent number
US07358400B2

Reaction notes

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