Diisopropylamine → 3-(4-Benzyloxyphenyl)2-ethoxy-3-hydroxy-2-methyl propanoic acid ethyl ester

HRID 987285ノート

反応式

HRID 987285 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][C:16](=[O:22])[CH:17]([O:19][CH2:20][CH3:21])[CH3:18])[CH3:14].[Li+].CC([N-]C(C)C)C.[CH2:31]([O:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[O:44])=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:13]([O:15][C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])([CH3:18])[CH:43]([C:42]1[CH:41]=[CH:40][C:39]([O:38][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:46][CH:45]=1)[OH:44])[CH3:14]

参加物

8

反応物 6

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 247453Ethyl 2-ethoxypropanoateHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

生成物 1

HCID 542946983-(4-Benzyloxyphenyl)2-ethoxy-3-hydroxy-2-methyl propanoic acid ethyl ester収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Di-isopropylamine (1.1 ml; 7.78 mmole) and dry tetrahydrofuran (35 ml) were mixed and cooled to −78° C. under nitrogen athmosphere. n-Butyllithium (1.6 M in hexane, 4.7 ml; 7.52 mmole) was added slowly and the reaction mixture was stirred for 15 minutes. 2-Ethoxypropionic acid ethyl ester was dissolved in a small amount of dry tetrahydrofuran and added slowly to the LDA mixture. The solution was stirred for 30 minutes at low temperature and then 4-benzyloxybenzaldehyde was added followed after 2 minutes by addition of saturated ammonium chloride solution (20 ml). The mixture was warmed to room temperature and the layers were separated. The aqueous phase was extracted twice with ether and the organic phases were combined and washed with hydrochloric acid (0.3 M, 100 ml) and brine dried with magnesium sulfate and evaporated. Purification of the residue by chromatography on silica gel using ethyl acetate: toluene (1:9) with triethylamine (0.1%) as eluant gave 1.63 g (68%) of 3-(4-benzyloxyphenyl)2-ethoxy-3-hydroxy-2-methyl propanoic acid ethyl ester.

後処理

  1. stirringThe solution was stirred for 30 minutes at low temperature
  2. temperatureThe mixture was warmed to room temperature
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted twice with ether
  5. washwashed with hydrochloric acid (0.3 M, 100 ml) and brine
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customPurification of the residue by chromatography on silica gel

出典と根拠

ORDレコード
ord-dc9e0e43e0ab4708aaa28adc30ea6c65
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

反応ノート

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