Hydrochloric Acid → methyl (S)-3-benzyloxymethyloxy-2-methylpropionate

HRID 654987ノート

反応式

HRID 654987 の反応式
[CH3:1][C@@H:2]([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].C(N(C(C)C)CC)(C)C.[CH2:18]([O:25][CH2:26]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>ClCCl.C(OCC)(=O)C>[CH2:18]([O:25][CH2:26][O:8][CH2:7][C@H:2]([CH3:1])[C:3]([O:5][CH3:6])=[O:4])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 137983Benzyl chloromethyl etherHCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

生成物 1

HCID 14348497methyl (S)-3-benzyloxymethyloxy-2-methylpropionate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Methyl (S)-(+)-2-methyl-3-hydroxypropionate (2.0 g; 16.9 mmole) and diisopropylethylamine (2.2 g; 17.1 mmole) were dissolved in dry dichloromethane (2 ml), and benzyloxymethyl chloride (2.7 g; 17.3 mmole) was dropwise added thereto, followed by stirring for 1 hour. 1N Hydrochloric acid (10 ml) and ethyl acetate (20 ml) were added thereto, and the aqueous layer was extracted with ethyl acetate. The extract was combined with the organic layer, washed with a sodium bicarbonate solution and water and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give methyl (S)-3-benzyloxymethyloxy-2-methylpropionate.

後処理

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washwashed with a sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a31efad7e8364d32bd45e1d90163e36e
出典データセット
uspto-grants-1992_07
特許番号
US05134231

反応ノート

読み込み中…