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

HRID 1186710ノート

反応式

HRID 1186710 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-6ae82d48280743afa0e42130cb6d5aee
出典データセット
uspto-grants-2014_03
特許番号
US08673911B2

反応ノート

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