Dimethyl Sulfoxide → (1S)-2-azido-1-(3-chlorophenyl)ethan-1-ol

HRID 470315Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:21])[CH2:9]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[N-:22]=[N+:23]=[N-:24].[Na+].CS(C)=O>O>[N:22]([CH2:9][C@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[OH:21])=[N+:23]=[N-:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester (16.34 g, 0.050 mol), sodium azide (6.50 g, 0.10 mol) and DMSO (50 ml) was stirred for 2 h at 80° C. Water (100 ml) was added, extracted with hexane-ether (1:1) mixture (2×150 ml). Combined extract was dried over Na2SO4, evaporated. The residue was separated on SiO2 (100 g), hexane-EtOAc, 0 to 20%. Colorless oil, 7.0 g, (0.035 mol, 71%). 1H NMR (300 MHz, DMSO) δ 7.46 (s, 1H), 7.36 (m, 3H), 5.95 (d, J=4.5 Hz, 1H), 4.82 (q, J=5.3 Hz, 1H), 3.35 (m, 2H).

Workup

extractionextracted with hexane-ether (1:1) mixture (2×150 ml)
extractionCombined extract
dry with materialwas dried over Na2SO4
customevaporated
customThe residue was separated on SiO2 (100 g), hexane-EtOAc, 0 to 20%

Sources & evidence

ORD record: ord-03c845c8f8e241dda1e361ba8e8d0426
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629147B2

Reaction notes

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