Water → HCID 54457404, compound

HRID 1108441Notes

Reaction equation

HRID 1108441 reaction equation
[N+:1]([CH2:4][CH:5](O)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[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:9]=[CH:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:13]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12093362HCID 12093362, compound

Product 1

HCID 54457404HCID 54457404, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4.89 g (18.1 mmol) of 1-nitro-4-(4-ethoxycarbonylphenyl)-2-butanol in 24 mL of dry methylene chloride at 0° C. was added 2.1 g (18.1 mmol) of methanesulfonyl chloride followed by addition of 3.66 g (36.2 mmol) of triethylamine. The mixture was stirred at 0° C. for 20 minutes, poured into 40 mL of water, extracted with 50 mL of methylene chloride, dried over anhydrous, and concentrated under reduced pressure. The residual solid was purified by column chromatography on silica gel, eluting with 1:9 ethyl acetate:hexanes, to afford 4.1 g (90%) of 1-nitro-4-(4-ethoxycarbonylphenyl)-1-butene as a light yellow solid: IR (KBr) 3112, 2982, 1713, 1647, 1610, 1519, 1424, 1417, 1353, 1277, 1178, 1104, 1021, 954, 935, 857, 766, 706 cm-1. 1H NMR (CDCl3) δ 8.02 (2H, d, J=8.5 Hz), 7.28 (1H, dt, J=14.0 and 7.5 Hz), 7.27 (2H, d, J=8.5 Hz), 6.98 (1H, d, J=14.0 Hz), 4.39 (2H, q, J=7.0 Hz), 2.92 (2H, t, J=7.5 Hz), 2.64 (2H, q, J=8.0 Hz), 1.42 (3H, t, J=7.0 Hz); 13C NMR (CDCl3) δ 166.55, 144.90, 140.91, 140.39, 130.23, 129.27, 128.49, 61.16, 34.12, 29.89, 14.52; EIMS m/z 249 (M+), 204, 202, 163, 135, 129, 118, 107, 90, 77; HRMS calc'd for C13H15NO4 249.1001 found 249.1029.

Workup

  1. extractionextracted with 50 mL of methylene chloride
  2. customdried over anhydrous, and
  3. concentrationconcentrated under reduced pressure
  4. customThe residual solid was purified by column chromatography on silica gel
  5. washeluting with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-9de8836518104be3aa242681117dabc4
Source dataset
uspto-grants-2000_05
Patent number
US06066732

Reaction notes

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