Pyridine → [2-(1-Bromocyclopropyl)ethoxy](tert-butyl)dimethylsilane

HRID 558192Notes

Reaction equation

HRID 558192 reaction equation
[Br:1][C:2]1([CH2:5][CH2:6][OH:7])[CH2:4][CH2:3]1.N1C=CC=CC=1.[Si:14](OS(C(F)(F)F)(=O)=O)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl>[Br:1][C:2]1([CH2:5][CH2:6][O:7][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 593863172-(1-Bromocyclopropyl)ethan-1-ol

Product 1

HCID 59386380[2-(1-Bromocyclopropyl)ethoxy](tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the cyclopropyl alcohol (Step A) (1.303 g, 7.95 mmoles) in 30 ml anhydrous DCM was added anhydrous pyridine (1.2 ml, 1.1736 g, 14.8 mmoles), TBSOTf (2.7 ml, 3.1077 g, 11.76 mol) and the solution was stirred at room temperature for 16 h. It was extracted with CHCl3/brine and the organic fraction was dried with MgSO4. The solvent was reduced and the crude product purified using flash-column chromatography (CHCl3/hexanes 1:10, Rf=0.4). Yield: 0.796 g, 36%. 1H-NMR (500 MHz, CDCl3): δ=3.95-3.75 (t, 2H), 1.95-1.85 (t, 2H), 1.15-1.05 (m, 2H), 0.95-0.80 (m, 11H), 0.15-0.05 (s, 6H).

Workup

  1. extractionIt was extracted with CHCl3/brine
  2. dry with materialthe organic fraction was dried with MgSO4
  3. customthe crude product purified

Sources & evidence

ORD record
ord-c6d1b25ca32649d39f096bcfa7c227bc
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

Loading…