Acetone → 4-Hydroxy-4-methyl-pent-2-ynoic acid ethyl ester

HRID 549389ノート

反応式

HRID 549389 の反応式
[CH2:1]([O:3][C:4](=[O:7])[C:5]#[CH:6])[CH3:2].C([Li])CCC.[CH3:13][C:14]([CH3:16])=[O:15]>O1CCCC1.CCOCC.CCCCC>[CH2:1]([O:3][C:4](=[O:7])[C:5]#[C:6][C:14]([OH:15])([CH3:16])[CH3:13])[CH3:2]

参加物

5

反応物 3

HCID 180AcetoneHCID 12182Ethyl propiolateHCID 178418339Butyllithium

生成物 1

HCID 112289264-Hydroxy-4-methyl-pent-2-ynoic acid ethyl ester収率 34.9%

試薬・触媒・溶媒 1

HCID 86634712Tetrahydrofuran ether pentane溶媒

実験手順

To a stirred solution of propynoic acid ethyl ester (20 mL, 197 mmol) in a mixture of 300 mL tetrahydrofuran:ether:pentane (4:1:1 by volume) cooled in a dry ice/isopropanol bath was added n-butyllithium (79 mL, 197 mmol, 2.5 M in hexanes) dropwise. After 15 minutes, anhydrous acetone (13.1 mL, 197 mmol) was slowly added. The reaction was kept below −78° C. for 8 h and quenched with an aqueous ammonium chloride solution, and the resulting mixture was stirred for 5 min. The reaction was warmed up to room temperature and extracted repeatedly with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, and the residue was purified via silica gel column chromatography (0-15% ethyl acetate in heptane) to give the title compound (10.75 g, 68.8 mmol) as a yellow oil.

後処理

  1. temperaturecooled in a dry ice/isopropanol bath
  2. waitThe reaction was kept below −78° C. for 8 h
  3. customquenched with an aqueous ammonium chloride solution
  4. extractionextracted repeatedly with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified via silica gel column chromatography (0-15% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-cfff57d0d91a4b35a6864bcaaee2e6b1
出典データセット
uspto-grants-2011_05
特許番号
US07943652B2

反応ノート

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