Dimethyl itaconate → Butanedioic acid, 2-methyl-, 1,4-dimethyl ester

HRID 1836746Notes

Reaction equation

HRID 1836746 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[CH2:3].[H][H].[1HH]>CO>[CH3:3][CH:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:1]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 69240Dimethyl itaconateHCID 5460631HCID 5460631, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15350Butanedioic acid, 2-methyl-, 1,4-dimethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.73 mg (0.0126 mmol) of [Rh(NBD)2]BF4 and 8.55 mg (0.0133 mmol) of B2a are placed in a flask provided with a magnetic stirrer and blanketed with argon by repeatedly evacuating the flask and flushing it with argon. 5 ml of degassed methanol are then added and the mixture is stirred for 15 minutes. 0.4 g (2.53 mmol) of dimethyl itaconate and 5 ml of degassed methanol are subsequently introduced into a 10 ml Schlenk flask filled with an argon atmosphere. Stirring is continued until a homogeneous solution is formed. The solution is injected by means of a steel capillary into a 180 ml glass reactor filled with argon. Finally, 1.05 bar of hydrogen are introduced in three flushing cycles (argon 1 bar/hydrogen 1 bar). The hydrogenation is started by switching on the stirrer and is carried out at 25° C. The course of the reaction is followed via the hydrogen consumption (pressure decrease in the hydrogen reservoir). After a reaction time of 20 hours, the conversion is found to be complete. The enantiomeric purity of dimethyl 2-methyl succinate is 94.6% of (R).

Workup

  1. customprovided with a magnetic stirrer
  2. customby repeatedly evacuating the flask
  3. customflushing it with argon
  4. addition5 ml of degassed methanol are then added
  5. additionfilled with an argon atmosphere
  6. stirringStirring
  7. customis formed
  8. additionfilled with argon
  9. customis carried out at 25° C
  10. customThe course of the reaction is followed via the hydrogen consumption (pressure decrease in the hydrogen reservoir)
  11. customAfter a reaction time of 20 hours

Sources & evidence

ORD record
ord-c21f091d4e254969b29663e4deff60b2
Source dataset
uspto-grants-2004_08
Patent number
US06777567B2

Reaction notes

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