Toluene → 2-(2-Methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid

HRID 1008290Notes

Reaction equation

HRID 1008290 reaction equation
[CH2:1]([C@@H:5]([C:11]([OH:13])=[O:12])[C@H:6]([OH:10])[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH3:4].[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)C[C:22]2=[O:23]>COC(OC)(OC)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:22][O:23][C:20]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:8][C:7](=[O:9])[CH:6]([CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:11]([OH:13])=[O:12])[O:10]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 60111363(2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid

Product 1

HCID 226668912-(2-Methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 69720Trimethyl orthobeznoateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (2S,3R)-3-(n-butyl)-2-hydroxysuccinic acid F-4 (300 mg, 1.58 mmol) and powdered molecular sieves (1 g) in trimethyl orthobenzoate (5 mL) and toluene (5 ml) was added 10-Camphorsulfonic acid (20 mg) and the reaction was heated at 110° C. under vacuum (20 torr) for 5 h. The solution was diluted with ethyl acetate, filtered through Celite and washed with brine, dried (Na2SO4) and then purified by silica gel chromatography to afford 1.2 mmol 2-(2-methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid I-1 (40%).

Workup

  1. filtrationfiltered through Celite
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b1564b975d7f4beab8168da06767de58
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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