Diethyl dimethylmalonate → 3-(4-Benzyloxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester

HRID 2212558

반응식

HRID 2212558 반응식
C([Li])(CC)C.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.[CH3:21][C:22]([CH3:33])([C:28](OCC)=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1COCC1>[CH2:26]([O:25][C:23](=[O:24])[C:22]([CH3:33])([CH3:21])[C:28]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)=[O:29])[CH3:27]

참가 물질

5

반응물 3

HCID 15382Diethyl dimethylmalonateHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 178418400CID 53628100

생성물 1

HCID 695965083-(4-Benzyloxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester수율 50.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

sec-Butyl lithium (5.85 mL, 7.6 mmol) was added to a solution of 1-bromo-4-benzyloxy-benzene (2.0 g, 7.6 mmol) in THF (10 mL) cooled to −78° C. under nitrogen. The reaction was stirred for 1 h and diethyl dimethylmalonate (4.29 g, 22.8 mmol) was added rapidly. This was stirred for an additional 0.5 h and then allowed to warm to room temperature. The reaction was partitioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by flash column chromatography (FCC) on silica gel eluting hexane:ethyl acetate (90: 10, v:v) to give 3-(4-benzyloxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester (1.25 g, 50%) as an oil. MS found: (M+H)+=327.

후처리

  1. stirringThis was stirred for an additional 0.5 h
  2. temperatureto warm to room temperature
  3. customThe reaction was partitioned between ethyl acetate and 1 N HCl
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe product was purified by flash column chromatography (FCC) on silica gel
  9. washeluting hexane:ethyl acetate (90: 10, v:v)

출처 및 근거

ORD 기록
ord-5359d81de4724a08af69adbf01961d95
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07102008B2

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