Diethyl Oxalate → HCID 178525999, compound

HRID 434776Notes

Reaction equation

HRID 434776 reaction equation
[O-]CC.[Na+].[C:5]([O:12]CC)(=[O:11])[C:6]([O:8]CC)=O.[OH:15][CH2:16][PH:17]([CH2:19][CH2:20]C(OCC)=O)=[O:18]>C1(C)C=CC=CC=1>[OH:15][CH2:16][PH:17]([CH2:19][CH2:20][C:6](=[O:8])[C:5]([OH:12])=[O:11])=[O:18]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 178472283HCID 178472283, compound

Product 1

HCID 178525999HCID 178525999, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A suspension of sodium ethoxide in toluene (50 ml) was prepared as in (a) above and to this was added diethyl oxalate (10.9 g) and a solution of ethyl 3-(hydroxymethylphosphinyl)propanoate (13.5 g) in toluene (75 ml). The mixture was stirred for 16 hours then extracted with water (4×60 ml). The extract was acidified with conc. hydrochloric acid (200 ml) and the acid solution refluxed for 2.5 hours. The crude product (8.8 g) was isolated as in part (a) and triturated with acetone to give the desired product (5.2 g).

Workup

  1. extractionthen extracted with water (4×60 ml)
  2. temperaturethe acid solution refluxed for 2.5 hours
  3. customThe crude product (8.8 g) was isolated as in part (a)
  4. customtriturated with acetone

Sources & evidence

ORD record
ord-14dc072f010f456ba96d54ba967683e2
Source dataset
uspto-grants-1983_08
Patent number
US04399287

Reaction notes

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