Ethyl orthoformate → HCID 44185486, compound

HRID 335522Notes

Reaction equation

HRID 335522 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
100 °C

Procedure

Process step c): 185.3 g (1.25 mol) of triethyl orthoformate were initially charged in a stirred vessel, the pressure in the vessel was reduced to 500 mbar and the triethyl orthoformate was heated to 100° C. 177.5 g (0.25 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 98° C. to 105° C. within 2 hours. Thereafter, the reaction mixture was stirred at 100° C. for further 3.5 hours. Within this post reaction time the pressure was further reduced to 300 mbar. During the whole reaction time low boiling compounds were removed by distillation under reduced pressure. The resulting suspension (191 g) comprised 16.7% (w/w) of the desired product (GC analysis, quantification with internal standard). The yield, based on ethyl difluoroacetate used, was 57.3%.

Workup

  1. additionwere added at 98° C. to 105° C. within 2 hours
  2. customWithin this post reaction time the pressure
  3. customDuring the whole reaction time low boiling compounds were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-c929787441fd4ba0a7e3d2a01709e0dc
Source dataset
uspto-grants-2014_11
Patent number
US08884028B2

Reaction notes

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