Triethylamine → Methanesulfonic acid 3-[4-((R)-2,2-dimethyl[1,3]dioxolan-4-ylmethoxy)-phenyl]-propylester

HRID 1183034Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=2)[CH2:4][O:3]1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(OCC)C>[CH3:1][C:2]1([CH3:19])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][O:18][S:28]([CH3:27])(=[O:30])=[O:29])=[CH:11][CH:10]=2)[CH2:4][O:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To (3-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-propan-1-ol (12.2 g, 46 mmol) in dry diethyl ether (150 mL) is added triethylamine (12.8 mL, 92 mmol). The mixture is cooled to 0° C. and treated dropwise with methanesulfonyl chloride (5.3 mL, 69 mmol). The reaction mixture is allowed to warm to RT and then stirring is continued for 3 h. The resulting mixture is washed with water (2×100 mL), saturated aqueous sodium hydrogen carbonate solution, brine then dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid.

Workup

temperatureto warm to RT
washThe resulting mixture is washed with water (2×100 mL), saturated aqueous sodium hydrogen carbonate solution, brine
dry with materialthen dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0174121dd39d481398960c94e85cc060
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664228B2

Reaction notes

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