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

HRID 2242566노트

반응식

HRID 2242566 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
25 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c773a155b7784747a0b5c3e7bae8bba1
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671226B2

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