1,2-Dimethoxyethane → (2-Methyl-5-{4-[3-(methylsulfanyl)propoxy]phenyl}furan-3-yl)methanol

HRID 1877195

反応式

HRID 1877195 の反応式
C([Si]([O:8][CH2:9][C:10]1[CH:14]=[C:13]([CH2:15]B2OCC(C)(C)CO2)[O:12][C:11]=1[CH3:24])(C)C)(C)(C)C.BrC1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][S:36][CH3:37])=[CH:28][CH:27]=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>[CH3:24][C:11]1[O:12][C:13]([C:15]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][S:36][CH3:37])=[CH:28][CH:27]=2)=[CH:14][C:10]=1[CH2:9][OH:8]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 68511011Tert-butyl({5-[(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)methyl]-2-methylfuran-3-yl}methoxy)dimethylsilaneHCID 685115371-Bromo-4-[3-(methylsulfanyl)propoxy]benzene

生成物 1

HCID 68507592(2-Methyl-5-{4-[3-(methylsulfanyl)propoxy]phenyl}furan-3-yl)methanol収率 88.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

A mixture of tert-butyl({5-[(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)methyl]-2-methylfuran-3-yl}methoxy)dimethylsilane (3.0 g), 1-bromo-4-[3-(methylsulfanyl)propoxy]benzene (2.8 g), tetrakis(triphenylphosphine)palladium(0) (0.5 g), 2N aqueous sodium carbonate solution (12 mL) and 1,2-dimethoxyethane (20 mL) was stirred overnight with refluxing 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 dissolved in tetrahydrofuran (20 mL), 1N tetrabutylammonium fluoride in tetrahydrofuran (10 mL) was added, and the mixture was stirred at room temperature for 2 hr. 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, purified by silica gel chromatography (0% ethyl acetate/hexane to 40% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (2.2 g, 84%) as a white crystal.

後処理

  1. temperaturewith refluxing 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. dissolutionThe residue was dissolved in tetrahydrofuran (20 mL)
  7. addition1N tetrabutylammonium fluoride in tetrahydrofuran (10 mL) was added
  8. stirringthe mixture was stirred at room temperature for 2 hr
  9. additionThe reaction mixture was poured into water
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over magnesium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. custompurified by silica gel chromatography (0% ethyl acetate/hexane to 40% ethyl acetate/hexane)
  15. customcrystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-9f411e3782e64de8882857efb7a9eb20
出典データセット
uspto-grants-2012_11
特許番号
US08309580B2

関連ノート

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