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

HRID 1186710Notes

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+].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]

Participants

Conditions

Temperature: -30 °C

Procedure

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)

Workup

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

Sources & evidence

ORD record: ord-6ae82d48280743afa0e42130cb6d5aee
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673911B2

Reaction notes

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