Ethyl orthoformate → HCID 44185486, compound

HRID 335523Notes

Reaction equation

HRID 335523 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])([O:5]CC)OCC.[F:11][CH:12]([F:21])[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=O>>[CH2:9]([O:8][C:1](=[O:5])/[C:14](=[CH:15]\[O:17][CH2:18][CH3:19])/[C:13](=[O:20])[CH:12]([F:21])[F:11])[CH3:10]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformate2×HCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 44185486HCID 44185486, compound

Conditions

Temperature
105 °C

Procedure

Process step c): 778.1 g (5.25 mol) of triethyl orthoformate were charged in a stirred vessel, the pressure within the vessel was slowly reduced to 310 mbar and the triethyl orthoformate was heated to 104° C. 121.1 g (0.175 mol-100% conversion in process steps a) and b) assumed) of ethyl 4,4-difluoroacetoacetate (in the form of a suspension coming from process step b)) were added at 103° C. to 104° C. within 2 hours. Thereafter, the reaction mixture was stirred at 105° C. for further 30 minutes. During the entire reaction time low boiling compounds were removed by distillation under reduced pressure. Afterwards, the suspension was cooled down to room temperature. The resulting suspension (761 g) comprised 4.36% (w/w) of the desired product (GC analysis, quantification with internal standard). This corresponds to an overall yield over the two synthetic steps of 85.4%, based on ethyl difluoroacetate used.

Workup

  1. additionwere added at 103° C. to 104° C. within 2 hours
  2. customDuring the entire reaction time low boiling compounds were removed by distillation under reduced pressure
  3. temperatureAfterwards, the suspension was cooled down to room temperature
  4. customThis corresponds to an overall yield over the two synthetic steps of 85.4%

Sources & evidence

ORD record
ord-68f46da9da33473abc1dd8d5a5227533
Source dataset
uspto-grants-2014_11
Patent number
US08884028B2

Reaction notes

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