Methanol → 1,1-Dimethoxybut-3-en-2-one

HRID 2064637Notes

Reaction equation

HRID 2064637 reaction equation
C[C:2]([CH3:5])=CN.[CH2:6]([O:8][C:9](C1C(C=O)=NNC=1)=O)C.[CH3:18][O-:19].[Na+].[CH3:21][OH:22]>>[CH3:18][O:19][CH:6]([O:8][CH3:9])[C:21](=[O:22])[CH:2]=[CH2:5]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 12400994DimethylvinylamineHCID 178469924HCID 178469924, compound

Product 1

HCID 224778181,1-Dimethoxybut-3-en-2-one

Procedure

The dimethylvinylamine from (i) was added to dry methanol (260 mL) and the mixture was then treated with pyruvic aldehyde dimethylacetal (51 mL), followed by a solution of sodium methoxide in methanol (30%, 81 mL), then stirred for 2 hours at ambient temperature, then heated at reflux temperature for another hour, then cooled and then filtered. The filtrate was evaporated to give 1,1-dimethoxy-but-3-en-2-one as a brown oil (96.8 g).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for another hour
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-53401d52dccc47dead4af490382ea846
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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