Water → (R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane

HRID 520491노트

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HRID 520491 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C@@H:19]1[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20]1.O>CN(C=O)C.CCCCC>[CH3:24][C:21]1([CH3:25])[O:20][C@H:19]([CH2:18][O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:23][O:22]1

참가 물질

7

반응물 4

HCID 962WaterHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 6930483(S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolane

생성물 1

HCID 58552880(R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane수율 52.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8003Pentane용매

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온도
160 °C

실험 절차

A mixture of 3-nitrophenol 102 (2.00 g, 14.4 mmol), potassium carbonate (4.96 g, 35.9 mmol) and (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane 103 (2.55 mL, 18.7 mmol) in DMF (20 mL) was heated in a microwave reactor at 160° C. for 4 h. The crude reaction mixture was poured into H2O and extracted with dichloromethane (3×15 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified by chromatography using ethyl acetate: pentane to obtain (R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane 104 (1.90 g, 52% yield) as an amber-colored oil.

후처리

  1. customThe crude reaction mixture
  2. extractionextracted with dichloromethane (3×15 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by chromatography

출처 및 근거

ORD 기록
ord-b8fe2cc778254508a22a2e03f536412c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326986B2

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