Ethyl orthoformate → HCID 44185486, compound

HRID 335524Notes

Reaction equation

HRID 335524 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
95 °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 170 mbar and the triethyl orthoformate was heated to 92° C. 134.3 g (0.35 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 92° C. to 95° C. within 4 hours. Thereafter, the reaction mixture was stirred at 95° C. for further 30 minutes. During the entire reaction time low boiling compounds were continuously removed by distillation under reduced pressure. Afterwards, the triethyl orthoformate was distilled by lowering the pressure accordingly. The resulting concentrated product suspension was cooled down to room temperature and 70.2 g of xylenes were added. The resulting suspension (178 g) comprised 40.0% (w/w) of the desired product (GC analysis, quantification with internal standard). This corresponds to an overall yield over the two synthetic steps of 91.6%, based on ethyl difluoroacetate used.

Workup

  1. additionwere added at 92° C. to 95° C. within 4 hours
  2. customDuring the entire reaction time low boiling compounds were continuously removed by distillation under reduced pressure
  3. distillationAfterwards, the triethyl orthoformate was distilled
  4. temperatureThe resulting concentrated product suspension was cooled down to room temperature
  5. addition70.2 g of xylenes were added
  6. customThis corresponds to an overall yield over the two synthetic steps of 91.6%

Sources & evidence

ORD record
ord-b14aff9a254d440ab6de1bb3421e2cea
Source dataset
uspto-grants-2014_11
Patent number
US08884028B2

Reaction notes

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