Water → HCID 86668978, compound

HRID 242199Notes

Reaction equation

HRID 242199 reaction equation
C(OP([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH:19]=O.O>CCCCCCC>[CH3:16][O:17][CH:18]([O:21][CH3:22])/[CH:19]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 107155Triethyl 2-phosphonopropionateHCID 162650Acetaldehyde, 2,2-dimethoxy-

Product 1

HCID 86668978HCID 86668978, compoundYield 121.4%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of ethyl 2-(diethoxyphosphoryl)propanoate (450 μL, 2.1 mmol) in heptane (5 mL) was added 2,2-dimethoxy acetaldehyde (60% in water, 1.0 mL, 4.2 mmol). The solution was stirred for 15 h at 60° C. After the reaction was cooled, water was added and the mixture was extracted with CH2Cl2 and filtered through a phase separator and a silica plug. Concentration under reduced pressure afforded (E)-ethyl 4,4-dimethoxy-2-methylbut-2-enoate (480 mg, >100%). The procedure was adapted from Tetrahedron 2002, 2533.

Workup

  1. temperatureAfter the reaction was cooled
  2. extractionthe mixture was extracted with CH2Cl2
  3. filtrationfiltered through a phase separator
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-c38c21e8c58842ed9d666e747c7836f2
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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