Acetic Anhydride → HCID 12764994, compound

HRID 1530273Notes

Reaction equation

HRID 1530273 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 12764994HCID 12764994, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-bb31c39bd2694ee5a3bb70e3361d788f
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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