Water → Methyl 2-(4-t-butylphenyl)propanoate

HRID 380961노트

반응식

HRID 380961 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[CH3:26]I.O>C1COCC1>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 605629Methyl p-tert-butylphenylacetateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 10704172Methyl 2-(4-t-butylphenyl)propanoate수율 101%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

23.3 mL of lithium bis(trimethylsilyl)amide (1.0 M, 23 mmols) was added dropwise to 4.75 g (23 mmols) of methyl 4-tert-butylphenylacetate in 100 mL of dry THF at −78° C. while stirring under nitrogen. The mixture was stirred at this temperature for 45 minutes, then 1.5 mL (24 mmol) methyl iodide was added dropwise and the solution was stirred for an additional 1 hour at −78° C. The mixture was poured into 200 mL of H2O and the desired product was extracted with 500 mL diethyl ether. The organic layer was backwashed once with 500 mL H2O, dried over K2CO3, and concentrated under reduced pressure to yield 5.12 g of a dark oil. The oil was purified via silica gel chromatography eluting with a solvent gradient of hexane to hexane/ethyl acetate 19:1. The fractions containing the desired product were combined and concentrated under reduced pressure to yield the title compound 2.65 g (53%).

후처리

  1. stirringThe mixture was stirred at this temperature for 45 minutes
  2. stirringthe solution was stirred for an additional 1 hour at −78° C
  3. extractionthe desired product was extracted with 500 mL diethyl ether
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e86f18a755c545ccaeab8ffc222fa6e2
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303816B1

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