Triethylamine → 3-Butyl-6-methyl-1,4-dioxane-2,5-dione

HRID 400351

反応式

HRID 400351 の反応式
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=[O:4].Br[CH:11]([CH3:15])[C:12](Br)=[O:13].C(N(CC)CC)C>CC(C)=O>[CH3:15][CH:11]1[O:4][C:3](=[O:5])[CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[O:1][C:12]1=[O:13]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 998242-Hydroxyhexanoic acid

生成物 1

HCID 579545563-Butyl-6-methyl-1,4-dioxane-2,5-dione収率 40%

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-hydroxyhexanoic acid (18.9 mmol) and 2.1 mL 2-bromopropionyl bromide (19.7 mmol) were stirred at 75° C. under nitrogen for 12 h. 150 mL acetone and 5.3 mL anhydrous triethylamine (38 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 300 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 5.05 (q, 1H), 4.90 (dd, 1H), 1.9-2.15 (br m, 2H), 1.68 (d), 1.65 (d), (3H, of 2 diastereoisomers), 1.3-1.6 (br m, 4H), 0.93 (t, 3H). 13C NMR (500 MHz, CDCl3): δ 167.54, 166.93, 166.25, 165.85, 75.79, 72.50, 72.24, 31.61, 29.70, 26.69, 26.42, 22.19, 21.97, 17.52, 15.81, 13.72, 13.66. ELEM. ANAL. Calcd. for C9H14O4: C, 58.06; H, 7.53. Found: C, 57.62; H, 7.60. Yield: 40%.

後処理

  1. filtrationAfter filtration of the triethylammonium bromide salts, acetone
  2. distillationwas distilled off
  3. dissolutionthe resulting mixture was dissolved in 300 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-ffa9a22035594fc392a93a72435f3cca
出典データセット
uspto-grants-2014_06
特許番号
US08741877B2

関連ノート

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