Acetyl chloride → Methyl 2-acetyl-3-phenylbutyrate

HRID 19719

Reaction equation

HRID 19719 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[C:13]1([CH:19]([CH3:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:26](Cl)(=[O:28])[CH3:27].C([O-])(O)=O.[Na+]>O1CCCC1.O>[C:26]([CH:20]([CH:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:25])[C:21]([O:23][CH3:24])=[O:22])(=[O:28])[CH3:27]

Participants

8

Reactant 5

HCID 6367Acetyl chlorideHCID 7912DiisopropylamineHCID 137945Methyl 3-phenylbutanoateHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 12561390Methyl 2-acetyl-3-phenylbutyrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

n-Butyllithium (2.5 M hexanes 12.4 ml, 30.9 mmol) is added to N,N-diisopropylamine (4.4 ml, 31.4 mmol) in tetrahydrofuran (THF, 50 ml) at 0° C. After 10 minutes, the resultant solution is transferred via cannula to a cooled (−78° C.) solution of methyl 3-phenylbutyrate (5.0 g, 28.05 mmol) in THF (50 ml). After 40 minutes, the resultant solution is transferred via cannula to a solution of acetyl chloride (19.15 ml) in THF (50 ml). The resultant mixture is stirred at −78° C. for 1.5 hours, then warmed to 0° C. after which water is added and the mixture is then poured into saturated NaHCO3 and extracted with EtOAc. The combined organic phases are washed with brine, dried (MgSO4) and evaporated. Purification by flash chromatography (12:1 EtOAc-hexane elution) affords the title compound. δH 1.3 (d J 7 3H), 2.3 (s 3H), 3.4 (s 3H), 3.6 (m 1H), 3.8 (m 1H), 7.2-7.4 (m 5H)

Workup

  1. waitAfter 40 minutes
  2. additionis added
  3. extractionextracted with EtOAc
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification
  8. washby flash chromatography (12:1 EtOAc-hexane elution)

Sources & evidence

ORD record
ord-f09846a5cb0b4d94b5b6987d8445cfd8
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Linked notes

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