Triethylamine → 3-(1-{[Tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propyl methanesulfonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Si:6]([O:13][C:14]1([CH2:20][CH2:21][CH2:22][OH:23])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:1][S:2]([O:23][CH2:22][CH2:21][CH2:20][C:14]1([O:13][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:4])=[O:3]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Methanesulfonyl chloride (2.1 mL, 27.4 mmol) was added dropwise to a solution of 3-(1-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propan-1-ol (6.80 g, 24.9 mmol) and triethylamine (4.20 mL, 29.9 mmol) in dichloromethane (100 mL) at 0° C. The solution was stirred for 2 h at 0° C., then was diluted with dichloromethane (20-25 mL) and saturated aqueous sodium bicarbonate (70 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (40 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to afford 3-(1-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propyl methanesulfonate as a pale oil that was used directly in the next step.
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted with dichloromethane (40 mL)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-012d85ac64fa47cdb49d6aa9b710fe1c
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884207B2
Reaction notes
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