Toluene → 1-(2-Methyl-1,3-dioxolan-2-yl)-2-(1-hydroxy-2,3,4,5-tetramethyl-2-cyclopentenyl)benzene

HRID 15694ノート

反応式

HRID 15694 の反応式
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2Br)[O:6][CH2:5][CH2:4][O:3]1.C([Li])CCC.[CH3:19][C:20]1[C:21](=[O:28])[CH:22]([CH3:27])[CH:23]([CH3:26])[C:24]=1[CH3:25].C1(C)C=CC=CC=1>O1CCCC1.CCCCCC.O>[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:21]2([OH:28])[CH:22]([CH3:27])[CH:23]([CH3:26])[C:24]([CH3:25])=[C:20]2[CH3:19])[O:6][CH2:5][CH2:4][O:3]1

参加物

8

反応物 4

HCID 1140TolueneHCID 410922,3,4,5-Tetramethyl-2-cyclopentenoneHCID 6152842-(2-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 178418339Butyllithium

生成物 1

HCID 230162251-(2-Methyl-1,3-dioxolan-2-yl)-2-(1-hydroxy-2,3,4,5-tetramethyl-2-cyclopentenyl)benzene収率 35.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
25 °C

実験手順

Under a nitrogen atmosphere, a solution of 2-(2-methyl-1,3-dioxolan-2-yl)-bromobenzene (1.22 g, 5.0 mmol) in tetrahydrofuran (7.3 g) was cooled to −10° C. and a solution of n-butyllithium in n-hexane (1.56 M, 3.4 mL) was added dropwise thereto. After keeping the temperature for 1 hr, a solution of 2,3,4,5-tetramethylcyclopentenone (0.73 g, 5.3 mmol) in tetrahydrofuran (4.9 g) was added dropwise to the mixture. After raising the temperature to 25° C., the mixture was stirred for 3 hrs. After quenching the reaction by addition of toluene and water, the aqueous layer was removed. The obtained organic layer was washed with saturated brine and then dried over sodium sulfate, and the solvent was removed. After concentration, the residue was washed with cooled hexane to give 1-(2-methyl-1,3-dioxolan-2-yl)-2-(1-hydroxy-2,3,4,5-tetramethyl-2-cyclopentenyl)benzene (0.53 g, yield 35.0%).

後処理

  1. customfor 1 hr
  2. customAfter quenching
  3. customthe reaction
  4. customthe aqueous layer was removed
  5. washThe obtained organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed
  8. concentrationAfter concentration
  9. washthe residue was washed with cooled hexane

出典と根拠

ORDレコード
ord-39da437e9a8f4fa7a9c615c95176064a
出典データセット
uspto-grants-2010_06
特許番号
US07732643B2

反応ノート

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