Chloromethyl Methyl Ether → ethyl 3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazole-5-carboxylate

HRID 507962노트

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HRID 507962 반응식
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)C(C)C)C.[CH3:40][O:41][CH2:42]Cl>O1CCCC1.O.CN(C)C=O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][O:24][CH2:40][O:41][CH3:42])=[CH:19][CH:18]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

9

반응물 5

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 2743509Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylateHCID 5107660[4-(Chloromethyl)phenyl]methanol

생성물 1

HCID 23157202ethyl 3-tert-butyl-1-{4-[(methoxymethoxy)methyl]benzyl}-1H-pyrazole-5-carboxylate수율 35.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

A mixture of ethyl 3-tert-butyl-1H-pyrazole-5-carboxylate (3.00 g, 15.3 mmol), [4-(chloromethyl)phenyl]methanol (2.50 g, 16.0 mmol), potassium carbonate (2.11 g, 15.3 mmol) and N,N-dimethylformamide (40 mL) was stirred at 70° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a yellow oil. To a solution of the obtained oil and N-ethyldiisopropylamine (8.0 mL, 46 mmol) in tetrahydrofuran (50 mL) was added chloromethyl methyl ether (4.40 mL, 46.3 mmol) at 0° C., and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to give the title compound (1.95 g. yield 35%) as a colorless oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow oil
  6. stirringthe mixture was stirred overnight at room temperature
  7. concentrationThe reaction mixture was concentrated
  8. customthe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-8f8f354f28b94a0cbb6585050c8f34e0
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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