Methyl iodide → HCID 66618863、化合物

HRID 406341ノート

反応式

HRID 406341 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][O:12][C:11](=[O:15])[CH2:10]2)=[CH:5][CH:4]=1.F[C:19](F)(F)C1C=CC(B(O)O)=CC=1.O1CCC=CC1=O.C([N-]C(C)C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C.IC>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH3:19][CH:10]1[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:8][CH:7]=2)[CH2:14][CH2:13][O:12][C:11]1=[O:15]

参加物

10

反応物 7

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 5206605,6-Dihydro-2H-pyran-2-oneHCID 2724682Lithium diisopropylamideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 66779092HCID 66779092、化合物HCID 178418339Butyllithium

生成物 1

HCID 66618863HCID 66618863、化合物収率 47.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 12679Hexamethylphosphoramide溶媒

実験手順

4-(4-Trifluoromethylphenyl)tetrahydropyran-2-one (995 mg) derived by the same method as in Preparation Example 2-10 from 4-(trifluoromethyl)phenylboronic acid (5.29 g) and 5,6-dihydro-2H-pyran-2-one was dissolved in tetrahydrofuran (10 mL). The solution was added dropwise at −78° C. to a lithium diisopropylamide solution previously prepared from n-butyllithium (3.91 mL) and diisopropylamine (1.46 mL) in tetrahydrofuran (30 mL). After stirring at the same temperature for 30 minutes, iodomethane (760 μL) and hexamethylphosphoramide (1.77 mL) were added and stirring was continued. After stirring for 30 minutes, the reaction solution was gradually heated to room temperature over three hours and 20 minutes. The reaction was terminated with saturated ammonium chloride aqueous solution. The organic layer was washed with brine and then dried over magnesium sulfate. Removal under reduced pressure gave an oil. The oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 50%) to obtain the title compound (500 mg).

後処理

  1. stirringstirring
  2. stirringAfter stirring for 30 minutes
  3. customThe reaction was terminated with saturated ammonium chloride aqueous solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customRemoval under reduced pressure
  7. customgave an oil
  8. customThe oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 50%)

出典と根拠

ORDレコード
ord-8f6513a7ad9c4e368fca45892ab30d2d
出典データセット
uspto-grants-2014_06
特許番号
US08754100B2

反応ノート

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