Diethyl Ether → (2-Cyclopropylthiazol-4-yl)methanol

HRID 1654211ノート

反応式

HRID 1654211 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[CH:12]1([C:15]2[S:16][CH:17]=[C:18]([C:20](OCC)=[O:21])[N:19]=2)[CH2:14][CH2:13]1>O.C(OCC)(=O)C>[CH:12]1([C:15]2[S:16][CH:17]=[C:18]([CH2:20][OH:21])[N:19]=2)[CH2:14][CH2:13]1

参加物

6

反応物 3

HCID 3283Diethyl Ether2 回HCID 18771956Ethyl 2-cyclopropylthiazole-4-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 20079576(2-Cyclopropylthiazol-4-yl)methanol収率 72.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of lithium aluminium hydride (0.32 g) and anhydrous ether (40 ml) was added dropwise an anhydrous ether (10 ml) solution of ethyl 2-cyclopropyl-4-thiazolecarboxylate (1.65 g), followed by stirring for one hour at room temperature. To the reaction mixture was added dropwise water (20 ml) under cooling with ice to decompose excess amount of the reducing agent. To the resultant mixture were added ethyl acetate (50 ml) and water (25 ml), followed by extraction with ethyl acetate. The organic layer was washed with water (25 ml) and a saturated aqueous solution of sodium chloride (25 ml), successively, followed by drying over magnesium sulfate. The solvent was distilled off, and the residue was subjected to a silica gel chromatography (2.5×30 cm), eluting with ethyl acetate-hexane (2:1). The desired fraction was concentrated to give 2-cyclopropyl-4-hydroxymethyl thiazole (0.94 g) as pale yellow needles. 1H-NMR (CDCl3) δ: 0.98~1.18(4H,m), 2.24~2.39(1H,m), 3.20(1H,bs.), 4.70(2H,d,J=5 Hz), 6.93(1H,s)

後処理

  1. temperatureunder cooling with ice
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water (25 ml)
  4. dry with materialby drying over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. washeluting with ethyl acetate-hexane (2:1)
  7. concentrationThe desired fraction was concentrated

出典と根拠

ORDレコード
ord-2ae6c6c4fa814cff82bd2663217298d3
出典データセット
uspto-grants-1995_04
特許番号
US05405861

反応ノート

読み込み中…