Hydrochloric Acid → HCID 21200437, compound

HRID 1870784Notes

Reaction equation

HRID 1870784 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:8][C:7]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:6]([F:20])[CH:5]=1.[CH:21](OCC)=[O:22].Cl>O1CCCC1>[Cl:3][C:4]1[C:9]([O:10][CH:11]([CH3:12])[CH3:13])=[CH:8][C:7]([CH:14]([CH:21]=[O:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:6]([F:20])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 54150401HCID 54150401, compound

Product 1

HCID 21200437HCID 21200437, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Then, 1.1 g of sodium hydride (60% in oil) was suspended in 50 ml of tetrahydrofuran, and the mixture was cooled to 5° C., to which a solution of 7.2 g of ethyl 4-chloro-2-fluoro-5-isopropoxyphenylacetate in 80 ml of tetrahydrofuran was slowly added dropwise. The mixture was stirred for 30 minutes with a gradual temperature increase to room temperature, to which 10 ml of ethyl formate was added at room temperature, followed by stirring for 3 hours. Then, the reaction mixture was cooled to 5° C., to which diluted hydrochloric acid was added. The reaction mixture was concentrated, and the residue was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 8.0 g of ethyl 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2-formylacetate.

Workup

  1. additionwas slowly added dropwise
  2. additionwas added at room temperature
  3. stirringby stirring for 3 hours
  4. additionwas added
  5. concentrationThe reaction mixture was concentrated
  6. additionthe residue was poured into water
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with saturated sodium chloride solution
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3e3f0ecc0c0f419da096ab23007e109b
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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