Benzyl Bromide → Methyl 2-(2-methoxyphenyl)-3-phenylpropanoate

HRID 60037

반응식

HRID 60037 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].C1COCC1.C([N-]C(C)C)(C)C.[Li+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCCCCCC.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:10]([O:12][CH3:13])=[O:11]

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 99590Methyl 2-methoxybenzeneacetateHCID 2724682Lithium diisopropylamide

생성물 1

HCID 66695010Methyl 2-(2-methoxyphenyl)-3-phenylpropanoate수율 35%

시약·촉매·용매 1

HCID 21263495Tetrahydrofuran heptane용매

반응 조건

온도
0 °C

실험 절차

A 500 mL round-bottom flask is charged with methyl 2-(2-methoxyphenyl)acetate (8.496 g, 47 mmol, 1 eq) and THF (200 mL). The homogeneous mixture is cooled to 0° C. in an ice bath. Lithium diisopropyl amide (23.5 mL of a 2.0M solution in heptane/THF) is added, maintaining a temperature less than 3° C. The reaction is stirred 45 minutes at this reduced temperature. Benzyl bromide (5.6 mL, 47 mmol, 1 eq) is added dropwise. The reaction is allowed to gradually warm to room temperature and is stirred for 18 hours. The reaction is quenched with 1N HCl and extracted 3 times with equal portions of EtOAc. The combined extracts are washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. The residue is purified over silica to afford 4.433 g (35%) of the desired compound. ESI+ MS 293 (M+Na).

후처리

  1. temperaturemaintaining a temperature less than 3° C
  2. temperatureto gradually warm to room temperature
  3. stirringis stirred for 18 hours
  4. customThe reaction is quenched with 1N HCl
  5. extractionextracted 3 times with equal portions of EtOAc
  6. washThe combined extracts are washed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified over silica

출처 및 근거

ORD 기록
ord-b727acaf84d04100872220a5c37a1ffb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440963B2

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