Water → (2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-one

HRID 703698

반응식

HRID 703698 반응식
[OH:1][C@H:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[C:8]1([CH2:14][CH2:15][CH:16]=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>ClCCl>[C:8]1([CH2:14][CH2:15][C@H:16]2[O:5][C:4](=[O:6])[CH2:3][C@@H:2]([CH3:7])[O:1]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7707BenzenepropanalHCID 921353-Hydroxybutanoic acid, (R)-HCID 22033616Pyridinium.p-toluenesulfonate

생성물 1

HCID 13741776(2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-one수율 63.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of (R)-3-hydroxybutanoic acid (7.8 g), 3-phenylpropionaldehyde (6.71 g) and pyridinium toluene-4-sulphonic acid (ca. 10 mmol %) in dichloromethane (300 ml) was stirred, under reflux, for 48 hours with removal of water. The reaction mixture was cooled to room temperature, washed three times with saturated sodium bicarbonate, dried (MgSO4) and evaporated under reduced pressure. The residue was crystallised from ether/pentane to give (2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-one (7.0 g), m.p. 49.7°-50.9° C.; [α]DR.T. =15.2(c=1.05; CHCl3).

후처리

  1. washwashed three times with saturated sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe residue was crystallised from ether/pentane

출처 및 근거

ORD 기록
ord-3bd0cb45f70b4fdf90c5a012c3b7f681
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04983766

연결된 노트

불러오는 중…