(R)-4-Benzyl-2-oxazolidinone → (R)-3-((E)-8-methylnon-6-enoyl)-4-benzyloxazolidin-2-one

HRID 1158128ノート

反応式

HRID 1158128 の反応式
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:19][CH:20]([CH3:30])/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>C1COCC1>[CH3:19][CH:20]([CH3:30])/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:9]1[C@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:28]

参加物

5

反応物 3

HCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 64423328-Methyl-6-nonenoyl chlorideHCID 178418339Butyllithium

生成物 1

HCID 59512586(R)-3-((E)-8-methylnon-6-enoyl)-4-benzyloxazolidin-2-one収率 85.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a cooled (−78° C.) solution of (R)-4-benzyloxazolidin-2-one (2.817 g, 15.899 mmol) in 40 mL of THF, was added n-BuLi (6.4 mL, 15.899 mmol, 2.5 M in hexane). The resulting mixture was stirred at −78° C. under N2 for 15 min. and then (E)-8-methylnon-6-enoyl chloride (3.000 g, 15.899 mmol) was added. After stirring at −78° C. for 1 h and then being warmed to room temperature under N2 for overnight, the reaction mixture was quenched with 80 mL of NH4Cl solution and extracted with dichloromethane (60 mL×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-30% ethyl acetate/hexanes to give the title compound as colorless oil (4.468 g, 85% yield). GC-MS: tR=6.2 min; m/z 329 (M+).

後処理

  1. stirringAfter stirring at −78° C. for 1 h
  2. temperaturebeing warmed to room temperature under N2 for overnight
  3. customthe reaction mixture was quenched with 80 mL of NH4Cl solution
  4. extractionextracted with dichloromethane (60 mL×3)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was isolated by Flash column chromatography (silica gel column)
  9. washeluting with 0-30% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-43be0c465c7e434da20269c201688535
出典データセット
uspto-grants-2010_10
特許番号
US07807720B2

反応ノート

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