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Water → Di-tert-butyl [4-(1,3-dioxolan-2-yl)-3-fluorophenyl](methyl)malonate

HRID 1172884
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HRID 1172884 반응식
[C:1]([O:5][C:6](=[O:27])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)=[C:17]([F:26])[CH:16]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].IC.[C:30](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:11]([O:10][C:8](=[O:9])[C:7]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)=[C:17]([F:26])[CH:16]=1)([CH3:30])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:27])([CH3:14])([CH3:13])[CH3:12]
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6

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HCID 962WaterHCID 6328Methyl iodide2회HCID 11430Potassium CarbonateHCID 57443964Di-tert-butyl [4-(1,3-dioxolan-2-yl)-3-fluorophenyl]malonate

생성물 1

HCID 57443965Di-tert-butyl [4-(1,3-dioxolan-2-yl)-3-fluorophenyl](methyl)malonate

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
70 °C

실험 절차

Di-tert-butyl[4-(1,3-dioxolan-2-yl)-3-fluorophenyl]malonate (2.45 g, 6.41 mmol), iodomethane (0.80 mL, 12.85 mmol) and potassium carbonate (1.78 g, 12.9 mmol) were suspended in DMF (10 mL) and heated at 70° C. for 3 hours in a sealed tube. A further portion of iodomethane was added (0.60 mL, 9.64 mmol) and heating continued at 75° C. for 3 hours. Room temperature was attained, H2O (150 mL) was added and the products extracted into Et2O (2×100 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC gave the clean product (orange oil). 1H NMR (CDCl3) δ 7.47 (t, J=8.1 Hz, 1H), 7.19 (dd, J=8.1, 1.8 Hz, 1H), 7.17 (dd, J=12.0, 1.8 Hz, 1H), 6.07 (s, 1H), 4.13 (m, 2H), 4.03 (m, 2H), 1.74 (s, 3H), 1.45 (s, 18H).

후처리

  1. temperatureheating
  2. customRoom temperature
  3. extractionthe products extracted into Et2O (2×100 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by MPLC
  8. customgave the clean product (orange oil)

출처 및 근거

ORD 기록
ord-78fa2697d70c41df90c7c7ee8672d93d
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834034B2

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