Dimethyl Sulfate → 2H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester

HRID 30846

反応式

HRID 30846 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[C:10](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 219302Oxane-4-carboxylic acid

生成物 1

HCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester収率 99.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Tetrahydro-2H-pyran-4-carboxylic acid (1.00 g, 7.68 mmol) was slowly added to a stirred suspension of anhydrous potassium carbonate (1.17 g, 8.45 mmol) in acetone (40 mL), followed by dimethyl sulfate (0.8 mL, 8.45 mmol). The mixture was stirred and heated for 3 h. The inorganic salts were then removed by filtration and washed with acetone, and the filtrate was dried and concentrated to give methyl tetrahydro-2H-pyran-4-carboxylate (1.1 g, 99%), which was used in the next step without further purification. GC-MS m/z 145 (MH+); 1H NMR (300 MHz, CDCl3) δ 11.70-1.80 (m, 4H), 2.47-2.52 (m, 1H), 3.34-3.43 (m, 2H), 3.65 (s, 3H), 3.88-3.95 (m, 2H).

後処理

  1. temperatureheated for 3 h
  2. customThe inorganic salts were then removed by filtration
  3. washwashed with acetone
  4. customthe filtrate was dried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-4eda794c23384bb1a87fbe1103d5afda
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

関連ノート

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