Sodium hydride → tert-Butyl (2-((tert-butyldimethylsilyl)oxy)ethyl)(prop-2-yn-1-yl)carbamate

HRID 1247599Notes

Reaction equation

HRID 1247599 reaction equation
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:2]#[CH:3].[H-].[Na+].Br[CH2:15][CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN1CCCC1=O>[Si:18]([O:17][CH2:16][CH2:15][N:4]([CH2:1][C:2]#[CH:3])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Product 1

HCID 11324466tert-Butyl (2-((tert-butyldimethylsilyl)oxy)ethyl)(prop-2-yn-1-yl)carbamate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The sub-titled compound was prepared from tert-butyl prop-2-yn-1-ylcarbamate (0.8 g), 60% sodium hydride (0.227 g), (2-bromoethoxy)-tert-butyldimethylsilane (1 ml) and anhydrous N-methyl-2-pyrrolidinone (4 ml) by the method of Example 2(ii). The crude product was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate (25:1) to afford (0.8 g).

Workup

  1. customThe crude product was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate (25:1)
  2. customto afford (0.8 g)

Sources & evidence

ORD record
ord-02cdf0af95e44dc8a1e835742a00a0c9
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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