1,2-Dimethoxyethane → Methyl 2-(methoxymethyl)-5-phenylfuran-3-carboxylate

HRID 1877099노트

반응식

HRID 1877099 반응식
Br[C:2]1[O:6][C:5]([CH2:7][O:8][CH3:9])=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:9][O:8][CH2:7][C:5]1[O:6][C:2]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:3][C:4]=1[C:10]([O:12][CH3:13])=[O:11]

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 68509863Methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylate

생성물 1

HCID 68514285Methyl 2-(methoxymethyl)-5-phenylfuran-3-carboxylate수율 87.5%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

A mixture of methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylate (3.7 g), phenylboronic acid (2.2 g), tetrakis(triphenylphosphine)palladium(0) (0.9 g), 2N aqueous sodium carbonate solution (18 mL) and 1,2-dimethoxyethane (30 mL) was stirred under reflux overnight under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 15% ethyl acetate/hexane) to give the title compound (3.2 g, 87%) as an oil.

후처리

  1. temperatureunder reflux overnight under an argon atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 15% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-5bf77e76eb744a489794937756cc753c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309580B2

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