Triethylamine → 2-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethyl methanesulfonate

HRID 1820312Notes

Reaction equation

HRID 1820312 reaction equation
C(N(CC)CC)C.[O:8]([CH2:26][CH2:27][C:28]1([CH2:34][CH2:35][OH:36])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:37][S:38]([O:36][CH2:35][CH2:34][C:28]1([CH2:27][CH2:26][O:8][Si:9]([C:22]([CH3:24])([CH3:25])[CH3:23])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 574278602-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanol

Product 1

HCID 574278622-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethyl methanesulfonateYield 104.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding triethylamine (2.20 mL, 15.8 mmol) to a solution of 2-[1-(2-tert-butyldiphenylsiloxyethyl)cyclohexyl]ethanol (3.24 g, 7.80 mmol) in methylene chloride (25 mL), methanesulfonyl chloride (0.91 mL, 11.7 mmol) was added dropwise while cooling on ice. The mixture was stirred at room temperature for 40 minutes, and then saturated aqueous sodium hydrogencarbonate (300 mL) was added, extraction was performed with chloroform and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure to obtain the title compound as a yellow oil (3.97 g).

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling on ice
  3. extractionextraction
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c0c41d351f34f43bb8d7ae019ded26b
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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