Water → 2-methyl-1-[3-methyl-5-(tetrahydro-2H-thiopyran-4-yloxy)-1-benzofuran-2-yl]propan-1-one

HRID 2091412

반응식

HRID 2091412 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[C:7]([CH3:15])[C:6]=2[CH:16]=1.CC1C=CC(S(O[CH:28]2[CH2:33][CH2:32][S:31][CH2:30][CH2:29]2)(=O)=O)=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C)C=O>[CH3:13][CH:11]([CH3:12])[C:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH:28]3[CH2:33][CH2:32][S:31][CH2:30][CH2:29]3)=[CH:16][C:6]=2[C:7]=1[CH3:15])=[O:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 62657Potassium Phosphate, Tribasic2회HCID 270400Tetrahydro-2h-thiopyran-4-yl 4-methylbenzenesulfonate2회HCID 667785551-(5-Hydroxy-3-methyl-1-benzofuran-2-yl)-2-methylpropan-1-one

생성물 1

HCID 667778112-methyl-1-[3-methyl-5-(tetrahydro-2H-thiopyran-4-yloxy)-1-benzofuran-2-yl]propan-1-one수율 61%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A solution of 1-(5-hydroxy-3-methyl-1-benzofuran-2-yl)-2-methylpropan-1-one (1.0 g) synthesized above, tetrahydro-2H-thiopyran-4-yl 4-methylbenzenesulfonate (2.99 g) and tripotassium phosphate (1.26 g) in N,N-dimethylformamide (10 mL) was stirred at 80° C. for 3 hr then at 100° C. for 14 hr. Tetrahydro-2H-thiopyran-4-yl 4-methylbenzenesulfonate (2.99 g) was added to the mixture, and the mixture was stirred at 100° C. for 20 min. Tripotassium phosphate (600 mg) was added to the mixture, and the mixture was stirred at 100° C. for 2 hr then at 120° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate 100:0-90:10, v/v) to give the title compound (886 mg, 61%) as an orange oil.

후처리

  1. waitat 100° C. for 14 hr
  2. stirringthe mixture was stirred at 100° C. for 20 min
  3. stirringthe mixture was stirred at 100° C. for 2 hr
  4. waitat 120° C. for 3 hr
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-f20c42aa3ee042799097f2c9983bbde5
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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