Water → 2-Chloro-5-(1,3-dioxolan-2-yl)benzofuran

HRID 2261106

反応式

HRID 2261106 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]=[CH:11][C:10]=2[CH:14]=1.C([Li])CCC.C1C(=O)N([Cl:27])C(=O)C1.O>C1COCC1.C(OCC)(=O)C>[Cl:27][C:12]1[O:13][C:9]2[CH:8]=[CH:7][C:6]([CH:2]3[O:3][CH2:4][CH2:5][O:1]3)=[CH:14][C:10]=2[CH:11]=1

参加物

7

反応物 4

HCID 962WaterHCID 31398ChlorosuccinimideHCID 552553255-(1,3-Dioxolan-2-yl)-1-benzofuranHCID 178418339Butyllithium

生成物 1

HCID 574696732-Chloro-5-(1,3-dioxolan-2-yl)benzofuran収率 82.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

5-[1,3]Dioxolan-2-yl-benzofuran (50 mg, 0.26 mmol) was dissolved in TIE (2 mL) and the solution was cooled down to −78° C. Butyl lithium (180 uL, 1.1 eq.) was added dropwise. This mixture was stirred 30 min at 25° C. Then the reaction mixture was cooled down to −78° C. and NCS (39 mg, 1.1 eq.) dissolved in 1 mL THF was added dropwise to the reaction mixture. After 1 h30 at −78° C. only small amount of starting material could be detected. The temperature was increased slowly to room temperature overnight. Water and ethyl acetate were added to the mixture and the aqueous layer was extracted 3 times. Combined organic phases was dried over MgSO4, filtrated and evaporated to give 2-Chloro-5-[1,3]dioxolan-2-yl-benzofuran (48.1 mg, 81%) sufficiently pure to be used in the next step.

後処理

  1. temperatureThen the reaction mixture was cooled down to −78° C.
  2. additionwas added dropwise to the reaction mixture
  3. customat −78° C.
  4. temperatureThe temperature was increased slowly to room temperature overnight
  5. extractionthe aqueous layer was extracted 3 times
  6. dry with materialCombined organic phases was dried over MgSO4
  7. filtrationfiltrated
  8. customevaporated

出典と根拠

ORDレコード
ord-fa8783c398214a318d539fbff946e87b
出典データセット
uspto-grants-2010_12
特許番号
US07846925B2

関連ノート

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