Methanesulfonic Acid → 2-ethyl-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid dimethyl ester

HRID 1193711Notes

Reaction equation

HRID 1193711 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[O:16])[CH2:14][CH3:15])[CH:7]=[CH:6]2.[CH3:17][O:18][C:19](=[O:28])[C@@H:20]([C@H:22]([C:24]([O:26][CH3:27])=[O:25])O)[OH:21].C(OC)(OC)OC.CS(O)(=O)=O>C([O-])([O-])=O.[Na+].[Na+]>[CH3:27][O:26][C:24]([C@H:22]1[C@H:20]([C:19]([O:18][CH3:17])=[O:28])[O:21][C:13]([CH2:14][CH3:15])([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)[O:16]1)=[O:25]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 9005Trimethyl orthoformateHCID 11851Dimethyl L-tartrateHCID 759131-(6-Methoxy-2-naphthalenyl)-1-propanone

Product 1

HCID 108616772-ethyl-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid dimethyl esterYield 63.6%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

1-(6-methoxy-2-naphthyl)-propan-1-one (46.5 g; 0.217 moles), L(+)tartaric acid dimethyl ester (300 g), trimethyl orthoformate (94 g; 0.887 moles) are gradually heated up to complete solution. Methanesulphonic acid (1.48 g; 0.0154 moles) is then added and the obtained solution is refluxed for 2 hours; it is cooled at room temperature and the reaction mixture is slowly added to a 10% solution of Na2CO3 (500 ml). It is extracted with methylene chloride and the organic extracts are repeatedly washed with water. The organic phase is dried on Na2SO4 and the solvent is evaporated under reduced pressure. The residue is crystallized from methanol (250 ml). The desired product is obtained (51.68 g; 0.138 moles; yield 63.6%) having the following characteristics:

Workup

  1. temperaturethe obtained solution is refluxed for 2 hours
  2. extractionIt is extracted with methylene chloride
  3. washthe organic extracts are repeatedly washed with water
  4. customThe organic phase is dried on Na2SO4
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is crystallized from methanol (250 ml)

Sources & evidence

ORD record
ord-099d9cd077d147df8cd7752129a246e3
Source dataset
uspto-grants-1989_03
Patent number
US04810819

Reaction notes

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