Gamma-Valerolactone → Pentanamide, N-heptyl-5-hydroxy-

HRID 374059

反応式

HRID 374059 の反応式
[C:1]1(=[O:7])O[CH:4]([CH3:5])[CH2:3][CH2:2]1.[CH2:8]([NH2:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CCCCCC.C(OCC)(=[O:24])C>C1(C)C=CC=CC=1>[CH2:8]([NH:15][C:5](=[O:24])[CH2:4][CH2:3][CH2:2][CH2:1][OH:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

6

反応物 4

HCID 7921Gamma-ValerolactoneHCID 8058HexaneHCID 81271-HeptanamineHCID 8857Ethyl Acetate

生成物 1

HCID 10262728Pentanamide, N-heptyl-5-hydroxy-

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Part A. A solution of γ-valerolactone (25.0 g, 0.249 mol) in toluene (50 mL) and n-heptylamine (35.96 g, 0.312 mol) was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate (300 mL), washed with 1N aqueous HCl (50 mL), water, brine, dried over magnesium sulfate and concentrated to give a white solid. The product was crystallized from ethyl ether:hexane to give N-heptyl-5-hydroxypentanamide (41.8 g, 0.194 mol) as white plates, mp 55°-6°. 1H NMR (CDCl3) δ6.06(bs,1H), 3.61(t,2H), 3.24(q,2H), 3.19(bs,1H), 2.19(t,2H), 1.80-1.23(m,14H), 0.866(t,3H).

後処理

  1. temperatureto reflux for 18 hours under a nitrogen atmosphere
  2. washwashed with 1N aqueous HCl (50 mL), water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a white solid
  6. customThe product was crystallized from ethyl ether

出典と根拠

ORDレコード
ord-b194f9f6266d49a58f6a356572f3a8c1
出典データセット
uspto-grants-1992_11
特許番号
US05166214

関連ノート

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