Triethylamine → 3-Methyl-6-hexyl-1,4-dioxane-2,5-dione

HRID 400352노트

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HRID 400352 반응식
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4].Br[CH:13]([CH3:17])[C:14](Br)=[O:15].C(N(CC)CC)C>CC(C)=O>[CH3:17][CH:13]1[O:4][C:3](=[O:5])[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[O:1][C:14]1=[O:15]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 94180Hydroxycaprylic Acid

생성물 1

HCID 450974043-Methyl-6-hexyl-1,4-dioxane-2,5-dione수율 45%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
60 °C

실험 절차

2.5 g 2-hydroxyoctanoic acid (15.6 mmol) and 1.75 mL 2-bromopropionyl bromide (16.3 mmol) were stirred at 80° C. under nitrogen for 12 h. 150 mL acetone and 4.35 mL anhydrous triethylamine (31 mmol) were added to the mixture and the solution was stirred for 3 h at 60° C. After filtration of the triethylammonium bromide salts, acetone was distilled off and the resulting mixture was dissolved in 250 mL ethyl acetate:hexane mixture (1:2). After filtration over silica gel the solvents were distilled off, and the remaining crude product was recrystallized from hexane. 1H NMR (500 MHz, CDCl3): δ 5.00 (q, 1H), 4.89 (dd, 1H), 1.9-2.15 (br m, 2H), 1.70 (d), 1.66 (d), (3H, of 2 diastereoisomers), 1.45-1.65 (br m, 2H), 1.25-1.40 (br m, 6H), 0.90 (t, 3H). 13C NMR (500 MHz, CDCl3): δ 167.53, 166.90. 166.26, 165.87, 75.80, 72.49, 72.25, 31.92, 31.45, 31.39, 30.00, 28.73, 28.50, 24.60, 24.29, 22.48, 22.44, 17.54, 15.83, 14.00. ELEM. ANAL. Calcd. for C11H18O4: C, 61.68; H, 8.41. Found: C, 61.63; H, 8.48. Yield: 45%.

후처리

  1. filtrationAfter filtration of the triethylammonium bromide salts, acetone
  2. distillationwas distilled off
  3. dissolutionthe resulting mixture was dissolved in 250 mL ethyl acetate
  4. filtrationAfter filtration over silica gel the solvents
  5. distillationwere distilled off
  6. customthe remaining crude product was recrystallized from hexane

출처 및 근거

ORD 기록
ord-24e9ff316efe499ab66eb4e0e88e6290
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741877B2

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