2,2-Dimethoxypropane → HCID 11174412, compound

HRID 459193Notes

Reaction equation

HRID 459193 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H: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)Cl.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@@H: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

Participants

6

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11818113(S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid

Product 1

HCID 11174412HCID 11174412, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

(S)-3-(4-Benzyloxy-phenyl)-2-hydroxy-propionic acid (2.0 g, 7.34 mmol), 2,2-dimethoxypropane (18.63 g, 0.179 mol) and pyridinium p-toluene sulfonate (0.92 g, 3.66 mmol) in chloroform (80 mL) was heated to reflux for 40 minutes under N2. The mixture was cooled, diluted with water, and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated in vacuo to give crude product that was purified by flash chromatography using 10:1 hexanes:acetone to afford the title compound (2.01 g, 88%). 1H-NMR (400 MHz, CDCl3) δ 7.43–7.29 (m, 5H), 7.17 (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), 3.12 (dd, 1H, J=14.617 Hz, J=4.40 Hz), 2.99 (dd, 1H, J=14.67 Hz, J=6.36 Hz), 1.49 (s, 3H), 1.36 (s, 3H). MS (ES+) m/z calc'd for C19H20O4 (M+NH4) 330. Found m/z 330.

Workup

  1. temperatureto reflux for 40 minutes under N2
  2. temperatureThe mixture was cooled
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give crude product that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-fad64f5c7ef643628c85a9d9d5368266
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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