Vinyl isobutyl ether → Methyl (R)-(+)-2-(1-Isobutoxyethoxy)propionate

HRID 2085621ノート

反応式

HRID 2085621 の反応式
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:23][CH3:24])(=[O:22])[C@@H:19]([CH3:21])[OH:20].[CH:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[CH2:26]>C(OCC)(=O)C>[CH2:28]([O:27][CH:25]([O:20][C@H:19]([CH3:21])[C:18]([O:23][CH3:24])=[O:22])[CH3:26])[CH:29]([CH3:31])[CH3:30]

参加物

5

反応物 3

HCID 7992Vinyl isobutyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 637514(+)-Methyl lactate

生成物 1

HCID 86759418Methyl (R)-(+)-2-(1-Isobutoxyethoxy)propionate収率 95.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A catalytic amount of pyridinium para-toluenesulfonate was added to 20.8 g (0.2 mole) of methyl (R)-(+)-lactate and 22.0 g (0.22 mole) of isobutyl vinyl ether. The resulting mixture was stirred at room temperature for 3 hours to give rise to a reaction. Thereto was added 100 ml of ethyl acetate, followed by washing with 100 ml of a saturated aqueous sodium hydrogen carbonate solution, 40 ml of water and 40 ml of a saturated aqueous sodium chloride solution in this order. The washed material was dried over anhydrous sodium sulfate and then subjected to vacuum distillation to remove the solvent. The resulting concentrate was subjected to distillation to obtain 38.8 g (yield: 95.1%) of an oily title compound (diastereomixture).

後処理

  1. customto give rise
  2. customto a reaction
  3. washby washing with 100 ml of a saturated aqueous sodium hydrogen carbonate solution, 40 ml of water and 40 ml of a saturated aqueous sodium chloride solution in this order
  4. dry with materialThe washed material was dried over anhydrous sodium sulfate
  5. distillationsubjected to vacuum distillation
  6. customto remove the solvent
  7. concentrationThe resulting concentrate
  8. distillationwas subjected to distillation

出典と根拠

ORDレコード
ord-71f452627c754e378973eed4e820586f
出典データセット
uspto-grants-2004_04
特許番号
US06720463B1

反応ノート

読み込み中…