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

HRID 2261108

반응식

HRID 2261108 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 552553255-(1,3-Dioxolan-2-yl)-1-benzofuranHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d4dfb744593846dfa53119146824ee3a
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846925B2

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