1,2,6-Hexanetriol → 1,3-Dioxolane-4-butanol, 2-phenyl-

HRID 225410

반응식

HRID 225410 반응식
[OH:1][CH2:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][OH:8].CO[CH:12](OC)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C.C(OCC)(=O)C>[C:13]1([CH:12]2[O:9][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][OH:8])[CH2:2][O:1]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 2

HCID 78231,2,6-HexanetriolHCID 62375Benzaldehyde dimethyl acetal

생성물 1

HCID 2366801,3-Dioxolane-4-butanol, 2-phenyl-수율 66.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a solution of 1,2,6-trihydroxyhexane (10.0 g, 74.6 mmol) and benzaldehyde dimethylacetal (15.0 g, 98.7 mmol) in dry DMF (10 mL) was added Amberlyst 15 (5.0 g). The mixture was stirred at 100° C. for 5 min, then cooled and filtered. The filtrate was concentrated and residue obtained was re-dissolved in ethyl acetate. After being washed with water and brine, the solution was dried over Na2SO4. The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate. Concentration of the proper fractions afforded 11.0 g (66%) of the title product (a mixture of diastereomers) as a colorless oil: 1H NMR (CDCl3, 300 MHz, ppm) 7.48 (m, 2H), 7.39 (m, 3H), 5.92 (s, 0.4H), 5.80 (s, 0.6H), 4.3-4.1 (m, 2H), 3.64 (m, 3H), 1.8-1.4 (m, 6H).

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customresidue obtained
  5. washAfter being washed with water and brine
  6. dry with materialthe solution was dried over Na2SO4
  7. customThe crude product obtained
  8. customafter evaporation of the solvent
  9. customwas chromatographed on silica eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-890a35a252d748c185edeceb8dcd8ed1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07556923B1

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