Hydrochloric Acid → 4-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one

HRID 1186710노트

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HRID 1186710 반응식
[C:1]([Si:5]([CH3:11])([CH3:10])[O:6][CH2:7][C:8]#[CH:9])([CH3:4])([CH3:3])[CH3:2].[Li+].CCC[CH2-].CON(C)[C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>C1COCC1>[Si:5]([O:6][CH2:7][C:8]#[C:9][C:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:27])([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:10])[CH3:11]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 61028n-Butyl lithiumHCID 569575N-Methoxy-N-methylbenzamideHCID 3445622Propargyloxy-t-butyldimethylsilane

생성물 1

HCID 108695084-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one수율 99.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-30 °C

실험 절차

To a solution of tert-Butyldimethyl(2-propynyloxy)silane 166 (7.99 mL, 39.4 mmol) in 80 mL of THF at −78° C. was added dropwise N-BUTYLLITHIUM (15.76 mL, 39.4 mmol). The resulting mixture was then warmed up slowly to −30° C. and stirred for 30 min. A solution of N-Methoxy-N-methylbenzamide 165 (5 mL, 32.8 mmol) in 5 mL of TIE was added dropwise and the solution was warmed slowly to room temperature and stirred 2 hours. Aqueous 5% HCl was added to quench the reaction and the product was extracted twice with ethyl acetate. The combined organic layers were washed with a saturated solution of bicarbonate and brine, dried over sodium sulfate and filtered. The solvents were removed in vacuo and the crude material was purified by ISCO (120 g column, 0-30% ethyl acetate in hexanes) to yield 99% of a yellow oil 167 (8.924 g)

후처리

  1. temperaturethe solution was warmed slowly to room temperature
  2. stirringstirred 2 hours
  3. customto quench
  4. customthe reaction
  5. extractionthe product was extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with a saturated solution of bicarbonate and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customThe solvents were removed in vacuo
  10. customthe crude material was purified by ISCO (120 g column, 0-30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-6ae82d48280743afa0e42130cb6d5aee
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673911B2

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