Citric Acid → 1-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethanol

HRID 1881871ノート

反応式

HRID 1881871 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([CH:11]=[O:12])=[CH:9][N:10]=1.[C:13](O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:12])[CH3:13])=[CH:9][N:10]=1

参加物

4

反応物 2

HCID 311Citric AcidHCID 593313182-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde

生成物 1

HCID 593314621-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethanol収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde (2.25 g) in tetrahydrofuran (20 mL) was slowly added a 1.13M methyllithium diethyl ether solution (12.0 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 30 min, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (1.96 g, yield 80%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). MS: 202 (MH+).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-e1a5fa507f894b018c62435913b5fc4d
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

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