Propargyl bromide → tert-Butyl (2-((tert-butyldimethylsilyl)oxy)ethyl)(prop-2-yn-1-yl)carbamate

HRID 1971672Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:19](Br)[C:20]#[CH:21].[H-].[Na+]>CN(C=O)C>[Si:1]([O:8][CH2:9][CH2:10][N:11]([CH2:21][C:20]#[CH:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 800 mg of 10b and 800 μl of propargyl bromide in 8 ml of DMF was treated with 300 mg of NaH (60% dispersion in oil) at 0° C. The mixture was stirred at 0° C. for 1 hr and then for 1 hr at RT (the reaction mixture turned gradually deep brown). Then the mixture was poured onto ice water and the product was extracted with ethyl acetate. The combined organic layers were washed with water, dried and concentrated. The crude material was chromatographed over silica gel, using a gradient of heptane/ethyl acetate as eluent, to provide 650 mg of 10c. Rf (heptane/ethyl acetate 8/2) 0.50.

Workup

waitfor 1 hr at RT (the reaction mixture turned gradually deep
additionThen the mixture was poured onto ice water
extractionthe product was extracted with ethyl acetate
washThe combined organic layers were washed with water
customdried
concentrationconcentrated
customThe crude material was chromatographed over silica gel

Sources & evidence

ORD record: ord-881eafc5275d4525847791069110b74c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431564B2

Reaction notes

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