Acetic acid, 2-phenoxy-, ethyl ester → HCID 15080405、化合物

HRID 477576

反応式

HRID 477576 の反応式
C([Li])CCC.[CH3:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8].[O:16]([CH2:23][C:24](OCC)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[C:10]1([S:7]([CH2:6][C:24](=[O:25])[CH2:23][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:9])=[O:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 17365Acetic acid, 2-phenoxy-, ethyl esterHCID 18369Methyl phenyl sulfoneHCID 178418339Butyllithium

生成物 1

HCID 15080405HCID 15080405、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

n-Butyllithium (8.5 ml, 1.6M in hexane) was added at -72° C. to a solution of methylphenyl sulfone (2.14 g, 13.7 mmol) in 80 ml of tetrahydrofuran. The reaction mixture was then allowed to warm slowly to -20° C. and maintained at this temperature for 25 minutes. It was then recooled to -72° C. and ethyl phenoxyacetate (1.48 g, 8.22 mmol) was added dropwise. The cooling bath was removed, the mixture was stirred at 20° C. for 14 hrs. and then poured into 100 ml of saturated NH4Cl and extracted with diethyl ether. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. The crude residue was purified by column chromatography (silica gel, methylene chloride) giving 1-phenylsulfonyl-2-oxo-3-phenoxypropane, the compound of formula (2a), 800 mg.

後処理

  1. temperaturemaintained at this temperature for 25 minutes
  2. customwas then recooled to -72° C.
  3. customThe cooling bath was removed
  4. additionand then poured into 100 ml of saturated NH4Cl
  5. extractionextracted with diethyl ether
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent removed under reduced pressure
  9. customThe crude residue was purified by column chromatography (silica gel, methylene chloride)

出典と根拠

ORDレコード
ord-2cd40da7323a4651b90ebe714304744b
出典データセット
uspto-grants-1989_12
特許番号
US04888358

関連ノート

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