Ethyl Acetate → HCID 131725094, compound

HRID 586687Notes

Reaction equation

HRID 586687 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[CH3:6][O:7][CH2:8][C@@H:9]1[C@H:11]([CH:12]=O)[C@:10]1([CH3:26])[C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:17]=[C:16]([CH:23]([CH3:25])[CH3:24])[CH:15]=1.[CH3:27][CH2:28][O:29][C:30]([CH3:32])=[O:31]>C1COCC1.CN1CCCN(C)C1=O.CCCCCC>[CH3:6][O:7][CH2:8][C@@H:9]1[C@H:11](/[CH:12]=[CH:1]/[C:2](/[CH3:3])=[CH:32]/[C:30]([O:29][CH2:28][CH3:27])=[O:31])[C@@:10]1([CH3:26])[C:14]1[CH:15]=[C:16]([CH:23]([CH3:25])[CH3:24])[CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 86595809HCID 86595809, compoundHCID 178418339Butyllithium

Product 1

HCID 131725094HCID 131725094, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

n-Butyl lithium in hexane (1.6 M, 0.56 mL, 0.89 mmol) was added to a solution of triethylphosphono-3-methyl-2E-butenoate (264 mg, 1.0 mmol) in 5 mL of THF and 3 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) at −78° C. After stirring for 5 min, a solution of Intermediate 45 (15 mg, 0.20 mmol) in 1 mL of TF was added by cannulation. The resulting solution was stirred at −7° C. for 2 h and then quenched with saturated NH4Cl. The mixture was then extracted with diethyl ether (3×5 mL), washed with brine (1×10 mL), dried (Na2SO4) and concentrated to give a crude colorless oil. Purification by column chromatography using 5%. EtOAc in hexane afforded the title compound (20 mg, 85% yield) as a white solid:

Workup

  1. stirringThe resulting solution was stirred at −7° C. for 2 h
  2. customquenched with saturated NH4Cl
  3. extractionThe mixture was then extracted with diethyl ether (3×5 mL)
  4. washwashed with brine (1×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a crude colorless oil
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-f8a8558e353d45b5886adfc84874ffb0
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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