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

HRID 1193711

反応式

HRID 1193711 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-099d9cd077d147df8cd7752129a246e3
出典データセット
uspto-grants-1989_03
特許番号
US04810819

関連ノート

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