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Acetic Acid → 3-[2-(4-Benzyloxy-phenyl)ethyl]-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

HRID 356524
ノート
印刷プレビュー

反応式

HRID 356524 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)C>C1COCC1>[C:17]([O:16][C:13](=[O:15])[CH2:14][C:37]([CH2:36][CH2:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:30][CH:31]=1)([OH:41])[CH:38]([CH3:39])[CH3:40])([CH3:20])([CH3:19])[CH3:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 187986371-(4-(Benzyloxy)phenyl)-4-methylpentan-3-oneHCID 178418339Butyllithium

生成物 1

HCID 539460993-[2-(4-Benzyloxy-phenyl)ethyl]-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-40 °C

実験手順

Diisopropylamine (44.8 mL, 320 mmol) in THF (125 mL) was cooled to -15° C. n-Butyllithium (1.6M, 200 mL, 320 mmol) was added over 20 minutes. The solution was cooled to -40° C. and stirred for 20 minutes. Tert-butyl acetate (43 mL, 320 mmol) in THF (90 mL) was added over 30 minutes and the reaction stirred for 30 minutes at -40° C. 1-(4-Benzyloxy-phenyl)-4-methyl-pentan-3-one (21.0 g, 100 mmol) from Example F in THF (125 mL) was added over 10 minutes and the reaction was stirred at -40° C. for 5 minutes. Acetic acid (40 mL, 700 mmol) was added and the reaction warmed to room temperature. The reaction was stripped to dryness and the product was partitioned between ethyl acetate and saturated NH4Cl. The organic layer was washed with water, 5% NaHCO3 and brine. It was dried (MgSO4) and concentrated to give the title compound.

後処理

  1. additionwas added over 20 minutes
  2. stirringthe reaction stirred for 30 minutes at -40° C
  3. stirringthe reaction was stirred at -40° C. for 5 minutes
  4. temperaturethe reaction warmed to room temperature
  5. customthe product was partitioned between ethyl acetate and saturated NH4Cl
  6. washThe organic layer was washed with water, 5% NaHCO3 and brine
  7. dry with materialIt was dried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-83dff350b0ad478abf769e3af813f061
出典データセット
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05834506

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート