Acetic Anhydride → HCID 12764994, compound
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
Conditions
- Temperature
- 10 °C
Procedure
To a solution of tert-butyldimethyl(prop-2-yn-1-yloxy)silane (15.1 g, 88.3%) in THF (300 mL), n-BuLi (67 mL, 105.9 mmol, 1.6 N in hexane) was added slowly at −78° C. After the addition was complete, the temperature was increased slowly to 10° C. over a period of 2 h. The reaction mixture was cooled again to −78° C. and BF3.OEt2 (14 mL, 105.9 mmol) added slowly and reaction mixture stirred at this temperature for 5 min. Acetic anhydride (11 mL, 115.6 mmol) was slowly added and the reaction was continued while temperature was allowed to rise to room temperature over a period of 2 h. After this time, reaction mass was quenched with 1N NaOH till pH 7-8 and biphasic solution was extracted with ethyl acetate. The organic layer was concentrated to obtain crude material which was further purified by column chromatography over silica gel to yield 5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-one (9.2 g, 52.6%).
Workup
- additionAfter the addition
- temperatureThe reaction mixture was cooled again to −78° C.
- customreaction mixture
- waitto rise to room temperature over a period of 2 h
- customAfter this time, reaction mass
- customwas quenched with 1N NaOH till pH 7-8 and biphasic solution
- extractionwas extracted with ethyl acetate
- concentrationThe organic layer was concentrated
- customto obtain crude material which
- customwas further purified by column chromatography over silica gel
Sources & evidence
- ORD record
- ord-fb2fb6b0227b4f319e32fbd14ffdfd29
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598167B1
Reaction notes
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