Dichloromethane → 2-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate
Reaction equation
ClCCl.[Cl:4][C:5]1[CH:6]=[C:7]([CH2:21][CH2:22][OH:23])[CH:8]=[C:9]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:10]=1[Cl:11].CCN(C(C)C)C(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>CCOCC>[CH3:33][S:34]([O:23][CH2:22][CH2:21][C:7]1[CH:8]=[C:9]([CH2:12][O:13][Si:14]([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:15])[CH3:16])[C:10]([Cl:11])=[C:5]([Cl:4])[CH:6]=1)(=[O:36])=[O:35]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a dichloromethane (0.11 M) solution of 2-[3,4-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethanol (1 eq.) from the previous step was added at 0° C. Hunig's base (1.5 eq.) and methanesulfonyl chloride (1.1 eq.). The resulting suspension was stirred at 0° C. for 30 min and at RT for 15 min. The reaction was then diluted with ether and quenched with 1N aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to give the title compound as a brown oil.
Workup
- customquenched with 1N aq. HCl
- customThe aqueous layer was separated
- extractionback-extracted with ether
- washThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-ba30d19d5c82457cabbcda5757a1e3a4
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889714B2
Reaction notes
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