Sulfuric Acid → HCID 58134741、化合物

HRID 1396094ノート

反応式

HRID 1396094 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-hydroxycyclobutylacetate (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 mixture 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-7a0d490d6ee54eada9721b69d7683825
出典データセット
uspto-grants-2014_12
特許番号
US08901112B2

反応ノート

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