Reaction #162405

Reaction equation

triisopropylsilyl triflate

(3,5-dichlorophenyl)methanol

2,6-lutidine

→

desired product

Yield 79.0%

[(3,5-dichlorobenzyl)oxy](triisopropyl)silane

Yield 79.0%

Solvents

water

methylene chloride

Conditions

Workup

1. 1
   Otherthe organic layer was separated
2. 2
   Washwashed with brine
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified by chromatography on silica gel
7. 7
   Washeluting with hexane

Procedure

To a solution of (3,5-dichlorophenyl)methanol (10.0 g, 56.5 mmol) in methylene chloride (100 mL) at 0° C. was added 2,6-lutidine (16.4 mL, 141 mmol) followed by triisopropylsilyl triflate (19.7 mL, 73.4 mmol), and was stirred at 0° C. for 2 hours. The reaction was diluted with water and the organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel, eluting with hexane to provide the desired product (14.8 g, 79%). LC/MS: 333 (M+H)+, 1H NMR (CDCl3) δ 7.23 (s, 3H), 4.78 (s, 2H), 1.18 (m, 3H), 1.03 (s, 18H).

Source