Triethylamine → 2-(2-(Methylsulfonyloxy)ethyl)-4-nitrobenzyl (methanesulfonate)

HRID 488368Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][CH2:13][OH:14].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][CH2:13][O:14][S:23]([CH3:22])(=[O:25])=[O:24])(=[O:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-[2-(hydroxymethyl)-5-nitrophenyl]ethanol (2.95 g, 14.96 mmol, J. Org. Chem., 1998, 63, 4116-4119) and triethylamine (6.26 mL, 44.9 mmol) in dry CH2Cl2 (60 mL) at 0° C. under N2 is treated with methanesulfonyl chloride (2.89 mL, 37.4 mmol) dropwise and stirred at 0° C. for 30 mins. The mixture is then diluted with CH2Cl2 (40 mL), washed with 1M aqueous HCl (20 mL), saturated aqueous NaHCO3 (20 mL) and brine (20 mL), dried over Na2SO4 and concentrated under reduced pressure to give the crude product which is chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with a gradient of EtOAc/heptane (30/70-70/30). Pooling and concentration of those fractions with an Rf=0.18 by TLC (EtOAc/hexane, 50/50) provides 4.58 g (87%) of the title compound as a white solid, mp 88-89° C.

Workup

washwashed with 1M aqueous HCl (20 mL), saturated aqueous NaHCO3 (20 mL) and brine (20 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customto give the crude product which
customis chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge
washeluting with a gradient of EtOAc/heptane (30/70-70/30)

Sources & evidence

ORD record: ord-0d7ccc49306e4e72b34bae40d3c05c16
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972286B2

Reaction notes

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