Citric Acid → 2-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde

HRID 1881870ノート

反応式

HRID 1881870 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][CH:8]=[CH:9][N:10]=1.CCCCCC.C([Li])CCC.CN(C)[CH:24]=[O:25].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([CH:24]=[O:25])=[CH:9][N:10]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 6228DimethylformamideHCID 152051582-(1,3-Dioxolan-2-yl)-1,3-thiazoleHCID 178418244HCID 178418244、化合物

生成物 1

HCID 593313182-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde収率 56.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole (10.00 g) in tetrahydrofuran (150 mL) was slowly added a 1.6M n-butyllithium hexane solution (44 mL) at −70° C. under a nitrogen atmosphere. The reaction mixture was stirred at −70° C. for 1 hr and N,N-dimethylformamide (14 g) was added. The reaction mixture was warmed to room temperature, 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 (6.64 g, yield 56%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). MS: 186 (MH+).

後処理

  1. temperatureThe reaction mixture was warmed to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-c289bddec93b4a229f84f7c1dc478c1c
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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