Water → 5-(1,3-Dioxolan-2-yl)-2-methylbenzofuran

HRID 2261108

反応式

HRID 2261108 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.[CH2:15]([Li])CCC.IC.O>C1COCC1.C(OCC)(=O)C>[CH3:15][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 6328Methyl iodideHCID 552553255-(1,3-Dioxolan-2-yl)-1-benzofuranHCID 178418339Butyllithium

生成物 1

HCID 574696765-(1,3-Dioxolan-2-yl)-2-methylbenzofuran収率 70%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回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 THF (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 iodomethane (18.1 uL, 1.1 eq.) dissolved in 1 mL THF was added dropwise to the reaction mixture. The temperature was increased slowly to room temperature overnight. Despite some starting material was detected, 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-methyl-5-[1,3]dioxolan-2-yl-benzofuran (41.2 mg, 70%) 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. temperatureThe temperature was increased slowly to room temperature overnight
  4. extractionthe aqueous layer was extracted 3 times
  5. dry with materialCombined organic phases was dried over MgSO4
  6. filtrationfiltrated
  7. customevaporated

出典と根拠

ORDレコード
ord-d4dfb744593846dfa53119146824ee3a
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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