4-Toluenesulfonyl chloride → 2-Phenyl-1,3-dioxan-5-yl 4-methylbenzenesulfonate

HRID 1011466Notes

Reaction equation

[C:1]1([CH:7]2[O:12][CH2:11][CH:10]([OH:13])[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:28][C:27]1[CH:29]=[CH:30][C:24]([S:21]([O:13][CH:10]2[CH2:11][O:12][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][CH2:9]2)(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 2 liter round bottom flask was added 2-phenyl-1,3-dioxan-5-ol (50 g, 277 mmol), triethyl amine (42.1 g, 416 mmol), DMAP (3.39 g, 27.7 mmol) and dichloromethane (1 L). The reaction was cooled to 0° C. To this solution was added tosyl chloride (58.2 g, 305 mmol) and the reaction was stirred overnight at RT. The reaction was poured onto water (800 mL) and extracted into DCM. The organic layers were combined and concentrated to dryness. The crude mixture was recrystallized from EtOAc:Hex to afford 88 g (96% yield) of a white solid. 1H NMR (CDCl3, 400 MHz), δ: 2.44 (3H, s), 4.09 (2H, dd, J=13.6, 2 Hz), 4.27 (2H, dd, J=13.6, 1.6 Hz), 4.51 (2H, pseudo t, J=1.6 Hz), 7.33-7.36 (5H, m), 7.44-7.45 (2H, m), 7.85 (2H, d, J=8.39 Hz). Mass Spec (lo-res): Calc'd for C17H18O5S: 334.09; found: 335.1 (M+H).

Workup

additionThe reaction was poured onto water (800 mL)
extractionextracted into DCM
concentrationconcentrated to dryness
customThe crude mixture was recrystallized from EtOAc

Sources & evidence

ORD record: ord-c849ca44a9294353a8ae3a8e215bc4c0
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977361B2

Reaction notes

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