Hexanoyl chloride → HCID 10858719、化合物

HRID 601715ノート

反応式

HRID 601715 の反応式
[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[NH:3]1.[Li]CCCC.[C:19](Cl)(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[C:19]([N:3]1[C@H:2]([CH3:1])[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4]1=[O:13])(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

5

反応物 3

HCID 67340Hexanoyl chlorideHCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 178418339Butyllithium

生成物 1

HCID 10858719HCID 10858719、化合物収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone (Aldrich Chemicals, 1.77 g, 10 mmol) in THF (100 mL) at −78° C. was added nBuLi (6.6 mL, 1.6 M in Hexane, 10.6 mmol) dropwise. After 10 minutes, hexanoyl chloride (1.68 mL, 12 mmol) was added. After 30 minutes the solution was allowed to warm to rt, at which time the reaction was quenched with saturated ammonium chloride solution. After 10 minutes, 1 M NaOH was added, and the mixture extracted 3 times with ethyl acetate. The combined organic layers were dried with MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (0% to 20% EtOAc/Hexane gradient) afforded pure product (1.98 g, 72%). 1H NMR (500 MHz, CDCl3) δ ppm 0.96-0.81 (m, 6H) 1.40-1.26 (m, 4H) 1.74-1.59 (m, 2H) 3.04-2.81 (m, 2H) 4.75 (dt, J=13.8, 6.7 Hz, 1H) 5.64 (d, J=7.32 Hz, 1H) 7.44-7.23 (m, 5H).

後処理

  1. waitAfter 30 minutes the solution was allowed
  2. customwas quenched with saturated ammonium chloride solution
  3. waitAfter 10 minutes
  4. addition1 M NaOH was added
  5. extractionthe mixture extracted 3 times with ethyl acetate
  6. dry with materialThe combined organic layers were dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8441dfd3b063402a8267ad515e43af76
出典データセット
uspto-grants-2011_03
特許番号
US07902218B2

反応ノート

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