Imidazole → Tert-butyl(chroman-4-yloxy)dimethylsilane

HRID 32064

Reaction equation

HRID 32064 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[O:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]([OH:19])[CH2:11][CH2:10]1.CN1CCOCC1.N1C=CN=C1>C(Cl)Cl>[C:1]([Si:5]([O:19][CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11]1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 79724-MethylmorpholineHCID 28928tert-Butyldimethylsilyl chlorideHCID 92890Chroman-4-ol

Product 1

HCID 18448670Tert-butyl(chroman-4-yloxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl-chloro-dimethyl-silane (10.54 g, 70 mmol) was added to a CH2Cl2 (200 mL) solution of 4-chromanol (10.00 g, 66.6 mmol), N-methylmorpholine (10.98 mL, 100 mmol) and imidazole (0.20 g, 3 mmol) at 0° C. The mixture was stirred for 3 days at RT. The reaction was diluted with CH2Cl2 (200 mL), washed with dilute HCl and H2O, dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound.

Workup

  1. washwashed with dilute HCl and H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fbaecf91b4346379115785c32c01434
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Linked notes

Loading…