Diethyl Ether → (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate

HRID 1400659Notes

Reaction equation

[CH3:1][C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].CCOCC>N1C=CC=CC=1>[CH3:17][C:16]1[CH:18]=[CH:19][C:13]([S:10]([O:8][CH2:7][C@@H:5]2[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol LIV (23.1 g, 0.175 mol) in pyridine (150 mL) at 0° C. was added tosyl chloride (44.5 g, 0.23 mol) in portions. The mixture was stirred for 7 h at 0° C. and was placed in a refrigerator for 18 h. Et2O (150 mL) was added and the mixture was washed with 1 N aqueous HCl (5×150 mL). The organic layer was washed with aqueous NaHCO3 (150 mL) and water (150 mL). The organic phase was dried over Na2SO4, filtered, concentrated and dried under vacuum. The crude product was purified by column chromatography on silica gel (1:1 Et2O:hexane) to afford (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate LV (42.1 g, 0.15 mol, 84%).

Workup

waitwas placed in a refrigerator for 18 h
washthe mixture was washed with 1 N aqueous HCl (5×150 mL)
washThe organic layer was washed with aqueous NaHCO3 (150 mL) and water (150 mL)
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customdried under vacuum
customThe crude product was purified by column chromatography on silica gel (1:1 Et2O:hexane)

Sources & evidence

ORD record: ord-fdb1a0428f374d35a06ff86e6ea3c19b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906868B2

Reaction notes

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