Hydrochloric Acid → HCID 13187242, compound

HRID 434488Notes

Reaction equation

HRID 434488 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].CC[O:9][CH2:10][CH3:11].[Cl:12][C:13]1[C:14]([CH2:22][PH:23](COCC)=[O:24])=C([CH:19]=[CH:20][CH:21]=1)C(O)=O.Cl>O>[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:1]2[C:14]=1[CH2:22][P:23]([O:9][CH2:10][CH3:11])(=[O:24])[CH2:3][C:2]2=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 23665647Potassium tert-butoxideHCID 178473682HCID 178473682, compound

Product 1

HCID 13187242HCID 13187242, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a rapidly stirred suspension of 16 g. (140 mmol.) of potassium t-butoxide in 600 mL. of anhydrous ether was added dropwise under nitrogen 11.7 g. (35 mmol.) of ethyl ester of 3-chloro-2-[(ethoxymethylphosphinyl)methyl]benzoic acid previously prepared as in Step A of Part B above in 50 mL. of ether. The reaction mixture was stirred for an additional 30 minutes. 100 mL. of water was added followed by concentrated hydrochloric acid to provide a pH of 7. The ether layer was separated, washed with brine and concentrated. Crystallization from hexane/methylene chloride gave 7.5 g. (83% yield) of 8-chloro-2-ethoxy-2,3-dihydro-2-oxo-4(1H)-isophosphinolinone as a representative species of compounds of formula (II).

Workup

  1. additionTo a rapidly stirred suspension of 16 g
  2. customto provide a pH of 7
  3. customThe ether layer was separated
  4. washwashed with brine
  5. concentrationconcentrated
  6. customCrystallization from hexane/methylene chloride
  7. customgave 7.5 g

Sources & evidence

ORD record
ord-474d08dc4e194ae180015b55645ddd75
Source dataset
uspto-grants-1983_08
Patent number
US04397790

Reaction notes

Loading…