Water → HCID 22916824, compound

HRID 1376829Notes

Reaction equation

HRID 1376829 reaction equation
Cl[CH:2]([Cl:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=[O:19]>O1CCCC1>[Cl:10][C:2]1([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[CH:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)[O:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 30164831,1-Dimethylethyl dichloroacetate

Product 1

HCID 22916824HCID 22916824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4 ml of tert.-butyl dichloroacetate in 15 ml of tetrahydrofuran and 2.6 ml of picolinaldehyde were mixed together and cooled to -20° C. to -25° C. Over 15 minutes at this temperature, 28 ml of potassium tert.-butylate in tetrahydrofuran at 0.9M/l were introduced and the mixture was allowed to warm up to ambient temperature. After 1 hour and 25 minutes, 25 ml of water were added, and extraction was effected with tetrahydrofuran. The organic phase was washed with water saturated with sodium chloride and then dried. The resulting solution containing 1,1-dimethylethyl 2-chloro-3-(2-pyridyl)oxirane carboxylate was held at -25° C. and used for the following step of the synthesis.

Workup

  1. temperaturecooled to -20° C. to -25° C
  2. extractionextraction
  3. washThe organic phase was washed with water saturated with sodium chloride
  4. customdried
  5. additionThe resulting solution containing 1,1-dimethylethyl 2-chloro-3-(2-pyridyl)oxirane carboxylate
  6. customwas held at -25° C.
  7. customused for the following step of the synthesis

Sources & evidence

ORD record
ord-78c7c661e58b4dfa9c21247ea89963e9
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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