Water → (4-Nitrobut-3-en-1-yl)benzene

HRID 1108444Notes

Reaction equation

[N+:1]([CH2:4][CH:5](O)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2].CS(Cl)(=O)=O.C(N(CC)CC)C.O>C(Cl)Cl>[N+:1]([CH:4]=[CH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5.85 g (30.0 mmol) of 1nitro-4-phenyl-2-butanol in 40 mL of dry methylene chloride at 0° C. was added 3.44 g (30.0 mmol) of methanesulfonyl chloride followed by addition of 6.07 g (60.0 mmol) of triethylamine. The mixture was stirred at 0° C. for 20 min, poured into 40 mL of water and extracted with 50 mL of methylene chloride. The extracts were dried over sodium sulfate, concentrated, and the residual solid purified by column chromatography (silica gel/ethyl acetate:hexanes 1:9) to afford 4.25 g (80%) of the product as a yellow oil. Since this material slowly decomposes at room temperature, it was used immediately for the next reaction: IR (neat) 3028, 2930, 1648, 1555, 1524, 1497, 1454, 1351, 1176, 953, 931, 750, 700 cm-1 ; 1H NMR (CDCl3) δ 2.63 (2H, q, J=7.0 Hz), 2.87 (2H, t, J=8.0 Hz), 7.00 (1H, dt, J=13.5 Hz), 7.21 (2H, d, J=7.5 Hz), 7.26-7.35 (4H, m); 13C NMR (CDCl3) 5 141.55,140.18, 139.74, 128.90, 128.46, 126.81, 34.19, 30.29; EIMS m/z 177 (M+) 60, 143, 133, 130, 115, 103, 91, 77; HRMS calc'd for C10H11NO2 177.0790, found 177.0802.

Workup

extractionextracted with 50 mL of methylene chloride
dry with materialThe extracts were dried over sodium sulfate
concentrationconcentrated
customthe residual solid purified by column chromatography (silica gel/ethyl acetate:hexanes 1:9)

Sources & evidence

ORD record: ord-86e4a4fc67544017a25d23eddd2c2c36
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06066732

Reaction notes

Loading…