Dichloromethane → 5-(4-Benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one

HRID 1985259노트

반응식

HRID 1985259 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:20])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:23](OC)([CH3:25])[CH3:24].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(Cl)Cl>C(Cl)(Cl)Cl.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]2[O:20][C:23]([CH3:25])([CH3:24])[O:18][C:17]2=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 107073143-(4-(Benzyloxy)phenyl)-2-hydroxypropanoic acid

생성물 1

HCID 184437075-(4-Benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

A mixture of 3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid (2.0 g, 7.34 mmol), 2,2-dimethoxypropane (18.63 g, 179 mmol) and pyridinium p-toluene sulfonate (0.92 g, 3.66 mmol) in CHCl3 (80 mL) was heated to reflux for 40 minutes under N2. The reaction was cooled and worked up extractively with CH2Cl2 and water. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 10:1 hexanes:acetone to afford 2.01 g (88%) 5-(4-benzyloxy-benzyl)-2,2-dimethyl-[1,3]dioxolan-4-one. Rf=0.53 (1:1 hexanes:acetone). 1H NMR (500 MHz, CDCl3) δ 7.43-7.35 (m, 4H), 7.34-7.29 (m, 1H), 7.16 (d, 2H, J=8.80 Hz), 6.91 (d, 2H, J=8.80 Hz), 5.04 (s, 2H), 4.61 (dd, 1H, J=6.36 Hz, J=4.40 Hz), 3.13 (dd, 1H, J=14.67 Hz, J=4.40 Hz), 2.99 (dd, 1H, J=14.67 Hz, J=4.40 Hz), 1.50 (s, 3H), 1.36 (s, 3H); MS (ES+) Calc'd for C19H20O4 (M+NH4) 330. Found m/z 330 (100%).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 40 minutes under N2
  3. temperatureThe reaction was cooled
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe solvent removed in vacuo
  6. customto afford crude product that
  7. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-3e7bd06d41d04f5180f60bd5a5edc025
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544812B2

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