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

HRID 374059

반응식

HRID 374059 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b194f9f6266d49a58f6a356572f3a8c1
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166214

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