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Dimethylformamide → 3-(1,3-dioxolan-2-yl)thiophene-2-carbaldehyde

HRID 1071627
ノート
印刷プレビュー

反応式

HRID 1071627 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][CH:7]=1.C([Li])CCC.CN([CH:19]=[O:20])C.[Cl-].[NH4+]>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[CH:19]=[O:20]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 3156302-(3-Thienyl)-1,3-dioxolaneHCID 178418339Butyllithium

生成物 1

HCID 115065723-(1,3-dioxolan-2-yl)thiophene-2-carbaldehyde収率 62.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

5.00 g (32.0 mmol) of 3-(1,3-dioxolan-2-yl)thiophene was dissolved in 100 ml of THF. 24.5 ml (1.5 mol/l) of n-butyllithium was added dropwise thereinto. After stirring for 0.5 hour, the mixture was cooled to −70° C., 3.10 ml (40.0 mmol) of DMF was added, and then the mixture was transferred to an ice bath. After stirring for about 2 hours, an aqueous saturated ammonium chloride was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give a crude product. The crude product was subjected to silica gel (ethyl acetate:hexane=1:2), to give 3.68 g (20.0 mmol, 62.4%) of the title compound as a yellow oil.

後処理

  1. customthe mixture was transferred to an ice bath
  2. stirringAfter stirring for about 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give a crude product

出典と根拠

ORDレコード
ord-1d443a390ba649ef88ae65cb63f68d26
出典データセット
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06906072B1

反応ノート

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