Acetic Anhydride → HCID 12764994、化合物

HRID 1530273ノート

反応式

HRID 1530273 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]CCCC.B(F)(F)F.[CH3:21][CH2:22][O:23]CC.C(OC(=O)C)(=O)C>C1COCC1>[Si:5]([O:6][CH2:7][C:8]#[C:9][C:22](=[O:23])[CH3:21])([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:10])[CH3:11]

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 8000Boron trifluoride etherateHCID 3445622tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silaneHCID 178418339Butyllithium

生成物 1

HCID 12764994HCID 12764994、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of tert-butyldimethyl(prop-2-yn-1-yloxy)silane (20.0 g, 116.9 mmol) in THF (400 mL) at −78° C. was added n-BuLi (90 mL, 140.0 mmol) and the reaction mixture was allowed to attain room temperature with in 2 h. Then the reaction mixture was cooled to −78° C. and borontrifluoride etherate (18 mL, 140.0 mmol) was added. After 10 minutes stirring acetic anhydride (15 mL, 153.0 mmol) was added and the reaction mixture was allowed to attain room temperature with in 2.5 h. Reaction was quenched with aqueous 1N NaOH solution and extracted with ethyl acetate (3 times). Combined organic layer was dried over sodium sulphate. Removal of the solvent under reduced pressure followed by solvent washings afforded C (13 g, 52%).

後処理

  1. customto attain room temperature with in 2 h
  2. additionwas added
  3. customto attain room temperature with in 2.5 h
  4. customReaction
  5. customwas quenched with aqueous 1N NaOH solution
  6. extractionextracted with ethyl acetate (3 times)
  7. dry with materialCombined organic layer was dried over sodium sulphate
  8. customRemoval of the solvent under reduced pressure
  9. customafforded C (13 g, 52%)

出典と根拠

ORDレコード
ord-bb31c39bd2694ee5a3bb70e3361d788f
出典データセット
uspto-grants-2015_07
特許番号
US09090562B2

反応ノート

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