Methyl Ethyl Ketone → Methyl 3-methylpent-2-enoate

HRID 1510125Notes

Reaction equation

HRID 1510125 reaction equation
C(OP([CH2:9][C:10]([O:12][CH3:13])=[O:11])(OCC)=O)C.C[O-].[Na+].[CH3:17][C:18](=O)[CH2:19][CH3:20]>O>[CH3:13][O:12][C:10](=[O:11])[CH:9]=[C:18]([CH3:17])[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 66113Methyl diethylphosphonoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 521288Methyl 3-methylpent-2-enoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 0° C. mixture of methyl diethylphosphonoacetate (12.7 ml, 69.3 mmol) and sodium methoxide (13.0 ml, 69.3 mmol) was added dropwise 2-butanone (5.81 ml, 69.3 mmol) over 30 min. After the addition, the mixture warmed to rt and stirred overnight. To the reaction was added 20 mL of H2O. The mixture was extracted with EtOAc (3 times). The combined organics were dried with MgSO4, filtered, and concentrated. The crude oil was distilled at 110° C. at 35 mmHg to give the desired product.

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with EtOAc (3 times)
  3. dry with materialThe combined organics were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. distillationThe crude oil was distilled at 110° C. at 35 mmHg

Sources & evidence

ORD record
ord-8a21c7b5779d480fad1ca79d24454987
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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