Water → HCID 178505292, compound
Reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C@@H:17]2[CH2:22][O:21][C@@H:20]([CH2:23][CH2:24][CH2:25][OH:26])[O:19][CH2:18]2)=[CH:9][CH:8]=1.C(N(CC)CC)C.O>ClCCl>[CH3:4][S:1]([O:26][CH2:25][CH2:24][CH2:23][C@H:20]1[O:21][CH2:22][C@H:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]([Cl:6])=[CH:8][CH:9]=2)[CH2:18][O:19]1)(=[O:3])=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 0.256 g (2.23 mmol) of mesyl chloride in 2 ml of dichloromethane is added, dropwise, to a solution of 0.530 g (1.72 mmol) of trans-3-[5-(4-chloronaphthalen-1-yl)-1,3-dioxan-2-yl]-1-propanol prepared in step 5.1 and of 0.48 ml (3.45 mmol) of triethylamine in 8 ml of dichloromethane cooled to 0° C. under an inert atmosphere. The reaction mixture is stirred at 0° C. for 1 hour. 25 ml of water and 50 ml of dichloromethane are added. The mixture is separated off after settling out and the aqueous phase is extracted with 50 ml of dichloromethane. The organic phases are washed with 25 ml of a saturated aqueous sodium chloride solution, drying is carried out over magnesium sulfate and concentration is carried out under vacuum, to obtain 0.66 g of product in the form of a white solid used without modification in the following step.
Workup
- customThe mixture is separated off
- extractionthe aqueous phase is extracted with 50 ml of dichloromethane
- washThe organic phases are washed with 25 ml of a saturated aqueous sodium chloride solution
- customdrying
- concentrationis carried out over magnesium sulfate and concentration
Sources & evidence
- ORD record
- ord-e68c3641a07c4716ad2ed5560adc8b74
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119687B2
Reaction notes
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