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

HRID 1257972

反応式

HRID 1257972 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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 tide 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).

後処理

  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

出典と根拠

ORDレコード
ord-3f4648cec5a649109e0f03d8cdef7429
出典データセット
uspto-grants-2013_06
特許番号
US08465921B2

関連ノート

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