Sodium Bicarbonate → Isopropyl(4-nitro-2-vinylphenyl)sulfane

HRID 1893136Notes

Reaction equation

HRID 1893136 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH:28]([S:31][C:32]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][C:33]=1[CH:34]=O)([CH3:30])[CH3:29].C(=O)(O)[O-].[Na+]>CCOCC>[CH:28]([S:31][C:32]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][C:33]=1[CH:34]=[CH2:2])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 579428652-[(1-Methylethyl)thio]-5-nitrobenzaldehyde

Product 1

HCID 68743034Isopropyl(4-nitro-2-vinylphenyl)sulfane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl triphenylphosphonium iodide (1.57 g, 3.88 mmol) was dissolved in 25 mL ether in a 50 mL round-bottomed flask at 0° C. under dry nitrogen. To the mixture was added in one portion potassium tert-butoxide (0.47 g, 4.16 mmol) and it was stirred for 10 min at room temperature. 2-(isopropylthio)-5-nitrobenzaldehyde (0.62 g, 2.77 mmol) was added in one portion at 0° C. and the reaction mixture was stirred for additional 4 h at room temperature. The mixture was added to 100 mL of saturated sodium bicarbonate solution, and then was extracted with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using 4:1 petroleum ether 60-80 and ether as eluent. Yield: 0.50 g, 81%, yellow oil. 1H NMR (200 MHz, CDCl3): δ 1.37 (d, J=6.6 Hz, 6H), 3.56 (septet, J=6.6 Hz, 1H), 5.50 (dd, J=0.9, 10.9 Hz, 1H), 5.80 (dd, J=0.9, 17.2 Hz, 1H), 7.09 (dd, J=10.9, 17.2 Hz, 1H), 7.40 (d, J=8.7 Hz, 1H), 8.04 (dd, J=2.5, 8.7 Hz, 1H), 8.30 (d, J=2.5 Hz, 1H) ppm. 13C NMR (50 MHz, CDCl3): δ 22.8, 37.1, 518.4, 120.9, 122.3, 128.2, 132.8, 138.4, 144.5, 145.5.

Workup

  1. stirringthe reaction mixture was stirred for additional 4 h at room temperature
  2. extractionwas extracted with 3×50 mL portions of ether
  3. dry with materialThe extracts were dried with magnesium sulfate
  4. customevaporated
  5. customThe crude product was further purified by chromatography on silica gel using 4:1 petroleum ether 60-80 and ether as eluent

Sources & evidence

ORD record
ord-d644dc96c1f84d9ea82e362fd98f3121
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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