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

HRID 400351

반응식

HRID 400351 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
60 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-ffa9a22035594fc392a93a72435f3cca
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741877B2

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