Acetyl chloride → Methyl 2-acetyl-3-phenylbutyrate

HRID 19719

반응식

HRID 19719 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

HCID 12561390Methyl 2-acetyl-3-phenylbutyrate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-f09846a5cb0b4d94b5b6987d8445cfd8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745462B2

연결된 노트

불러오는 중…