Chloroform → 2-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanol

HRID 2223854Notes

Reaction equation

HRID 2223854 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([CH2:10][CH2:11][OH:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[C:20]([Si:24]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)Cl)([CH3:23])([CH3:22])[CH3:21].C(Cl)(Cl)Cl>ClCCl>[O:1]([CH2:2][CH2:3][C:4]1([CH2:10][CH2:11][OH:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 76657Cyclohexane-1,1-diethanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 574278602-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (6.41 g) in dichloromethane (170 mL) were added triethylamine (6.74 mL) and tert-butyldiphenylchlorosilane (11.1 mL) at room temperature. After stirring the solution at room temperature for 18 hours, chloroform was added to the solution, and it was washed in turn with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=85:15) to give the title compound (10.97 g).

Workup

  1. washwas washed in turn with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialThe solution was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-405bd573b94d4a1ba7f60b693790c78d
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

Loading…