Sulfuric Acid → HCID 58134741、化合物

HRID 444784ノート

反応式

HRID 444784 の反応式
OS(O)(=O)=O.O[C:7]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9][CH2:8]1.[C:17](#[N:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-:25].[Na+]>>[C:17]([NH:24][C:7]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9][CH2:8]1)(=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 4

HCID 1118Sulfuric AcidHCID 7505BenzonitrileHCID 14798Sodium HydroxideHCID 58134840ETHYL 2-(1-HYDROXYCYCLOBUTYL)ACETATE

生成物 1

HCID 58134741HCID 58134741、化合物収率 51%

実験手順

H2SO4 (2.20 mL, 41.3 mmol) was slowly added to a mixture of ethyl (1-hydroxycyclobutyl)acetate (6.45 g, 40.8 mmol) and benzonitrile (40 mL, 0.392 mol) at room temperature. The mixture was stirred for 1 hour at room temperature, then for an additional hour at 80° C. The mixture was cooled in an ice-water bath, and 2N NaOH solution was added until the solution reached pH=7. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (AcOEt:Hexane=5:1) of the residue gave the title compound as a colorless solid (5.40 g, 51%). 1H-NMR (400 MHz, CDCl3) δ 1.22 (3H, t, J=7.3 Hz), 1.84-2.07 (2H, m), 2.22-2.32 (2H, m), 2.44-2.55 (2H, m), 3.05 (2H, s), 4.11 (2H, q, J=7.3 Hz), 6.73 (1H, s), 7.39-7.52 (3H, m), 7.72-7.79 (2H, m).

後処理

  1. waitfor an additional hour at 80° C
  2. temperatureThe mixture was cooled in an ice-water bath
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-347112745b1f4b46a82c1ec295f9e14f
出典データセット
uspto-grants-2013_07
特許番号
US08476261B2

反応ノート

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