(3E)-4-Methoxy-3-buten-2-one → HCID 178495555, compound

HRID 2066786Notes

Reaction equation

HRID 2066786 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][O:12]/[CH:13]=[CH:14]/[C:15](=[O:17])[CH3:16].[CH3:18][C:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1>C1COCC1>[OH:23]/[C:22](/[C:19]1([CH3:18])[CH2:21][CH2:20]1)=[CH:16]\[C:15](=[O:17])/[CH:14]=[CH:13]/[O:12][CH3:11]

Participants

5

Reactant 3

HCID 639675(3E)-4-Methoxy-3-buten-2-oneHCID 2733832Lithium HexamethyldisilazideHCID 127899391-Methylcyclopropane-1-carbonyl chloride

Product 1

HCID 178495555HCID 178495555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiHMDS (1M in THF, 845 mmol) was added dropwise to a solution of trans-4-methoxy-3-buten-2-one [51731-17-0] (845 mmol) in THF (2 L) at −78° C. After stirring for 15 min, a solution of 1-methyl-cyclopropanecarbonyl chloride [16480-05-0] (407 mmol) in THF (100 mL) was added. The resulting mixture was allowed to warm to rt over 2.5 h and then quenched by addition of a saturated solution of NH4Cl. The mixture was extracted with Et2O (2×). The combined organic phases were successively washed with a saturated solution of NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a yellow solid. ESI-MS: [M+H]+ 183; TLC: Rf=0.29 (9:1 Hex/EtOAc).

Workup

  1. customquenched by addition of a saturated solution of NH4Cl
  2. extractionThe mixture was extracted with Et2O (2×)
  3. washThe combined organic phases were successively washed with a saturated solution of NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-387a744e5bda47a3bde3e31d506fa081
Source dataset
uspto-grants-2012_10
Patent number
US08293753B2

Reaction notes

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