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

HRID 400352

反応式

HRID 400352 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
60 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-24e9ff316efe499ab66eb4e0e88e6290
出典データセット
uspto-grants-2014_06
特許番号
US08741877B2

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