3-Methylbenzaldehyde → Ethyl 3-methylcinnamate

HRID 546300노트

반응식

HRID 546300 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:13][C:14](=[O:30])[CH2:15]P(OCC(F)(F)F)(OCC(F)(F)F)=O)[CH3:12].C1OCCOCCOCCOCCOCCOC1.[C:49]1([CH3:57])[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]=O)[CH:50]=1>C1COCC1>[CH2:11]([O:13][C:14](=[O:30])[CH:15]=[CH:57][C:49]1[CH:50]=[C:51]([CH3:55])[CH:52]=[CH:53][CH:54]=1)[CH3:12]

참가 물질

6

반응물 4

HCID 121053-MethylbenzaldehydeHCID 2855718-Crown-6HCID 3251421Potassium bis(trimethylsilyl)amideHCID 11759356Ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate

생성물 1

HCID 589327Ethyl 3-methylcinnamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

KHMDS (4.0 g, 20.0 mmol) was added to a solution of ethyl[bis(2,2,2-trifluoro-ethoxy)phosphinyl]acetate (4.7 mL, 20.0 mmol) and 18-crown-6 (10.6 g, 40.0 mmol) in THF (200 mL) at −78° C., and stirred for 30 minutes. m-Tolualdehyde (2.1 mL, 18 mmol) was added and the reaction mixture was stirred for 3 hours from −78° C. to room temperature. The reaction was quenched with aqueous hydrochloric acid (1 M solution, 100 mL), and the product was extracted with EtOAc (3×100 mL). The organic extracts were washed with brine (100 mL), dried over MgSO4, and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C12H14O2+H: 191, observed: 191.

후처리

  1. stirringthe reaction mixture was stirred for 3 hours from −78° C. to room temperature
  2. customThe reaction was quenched with aqueous hydrochloric acid (1 M solution, 100 mL)
  3. extractionthe product was extracted with EtOAc (3×100 mL)
  4. washThe organic extracts were washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d2853e17c7fd4b75901c6050fdb309af
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935830B2

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