Imidazole → (1,4-Dioxaspiro[4.5]decan-8-ylmethoxy)(tert-butyl)dimethylsilane

HRID 1093107Notes

Reaction equation

HRID 1093107 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanol

Product 1

HCID 57904787(1,4-Dioxaspiro[4.5]decan-8-ylmethoxy)(tert-butyl)dimethylsilaneYield 101.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-ylmethanol (8.60 g, 49.9 mmol) and imidazole (8.50 g, 125 mmol) in DMF (50 mL) was added tert-butyldimethylsilyl chloride (9.03 g, 59.9 mmol), and the mixture stirred at room temp. for 18 hours. The mixture was concentrated in vacuo and the residue redissolved in ethyl acetate (20 mL), washed with water followed by brine, then dried (Na2SO4), and concentrated in vacuo to provide the title compound (14.5 g, 50.6 mmol, 101% yield) as a clear oil: LCMS: m/z 287 (M+H); 1H NMR (500 MHz, CDCl3) δ ppm 0.01 (6H, s), 0.86 (9H, s),1.14-1.26 (2H, m), 1.45-1.54 (3H, m), 1.67-1.82 (4H, m), 3.40 (2H, d, J=6.7 Hz), 3.91 (4H, s); 13C NMR (126 MHz, CDCl3) δ ppm-5.25, 18.5, 26.1, 26.9, 34.3, 39.2, 64.3, 68.0, 109.3.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue redissolved in ethyl acetate (20 mL)
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5fc064a2e5d4db2abe34c51cd9f5c37
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

Loading…