Water → tert-Butyl-2-(1-ethylcyclohexyl)ethoxydiphenylsilane

HRID 1820313Notes

Reaction equation

HRID 1820313 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CS(O[CH2:12][CH2:13][C:14]1([CH2:20][CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=O)=O.O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[C:36]([Si:23]([O:22][CH2:21][CH2:20][C:14]1([CH2:13][CH3:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 574278622-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethyl methanesulfonate

Product 1

HCID 23109888tert-Butyl-2-(1-ethylcyclohexyl)ethoxydiphenylsilaneYield 98.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

After suspending lithium aluminum hydride (0.30 g, 7.80 mmol) in tetrahydrofuran (15 mL), a solution of 2-[1-(2-tert-butyldiphenylsiloxyethyl)cyclohexyl]ethyl methanesulfonate (3.97 g, 7.80 mmol) in tetrahydrofuran (10 mL) was added dropwise at room temperature over a period of 10 minutes. After stirring for an additional 10 minutes, the mixture was heated to reflux for 45 minutes. Water (0.30 mL), 15% aqueous sodium hydroxide (0.30 mL) and water (0.90 mL) were added dropwise in that order while cooling on ice, diethyl ether (25 mL) was added and the mixture was stirred for 16 hours, and then celite was added and stirring was continued for 1 hour prior to filtration. The filtrate was concentrated under reduced pressure to obtain the title compound as a colorless oil (3.02 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 45 minutes
  3. additionwas added
  4. stirringthe mixture was stirred for 16 hours
  5. additioncelite was added
  6. stirringstirring
  7. waitwas continued for 1 hour
  8. filtrationto filtration
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4470b11521024481a5a75883d706aba8
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

Loading…