Nitromethane → HCID 11413010, compound

HRID 1354585Notes

Reaction equation

HRID 1354585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].S([O-])([O-])(=O)=O.[Mg+2].CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C.[N+:37]([CH3:40])([O-:39])=[O:38]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:40][N+:37]([O-:39])=[O:38])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 114773-ChlorobenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 3856267tert-Butylimino-tri(pyrrolidino)phosphorane

Product 1

HCID 11413010HCID 11413010, compoundYield 100%

Procedure

To a solution of 3-chloro-benzaldehyde (20 g, 0.142 mol) in nitromethane (100 mL) were added magnesium sulfate (37.6 g, 0.312 mol) and phosphazene base P1-t-bu-tris(tetramethylene) (4.43 g, 0.014 mol). The reaction mixture was stirred at room temperature for 2 h. After concentration in vacuo, the residue was purified by flash chromatography (25% EtOAc/hexane) to yield the title compound (26.4 g, 100%) as a green-yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 7.53 (1H, s), 7.35–7.42 (3H, m), 6.23 (1H, broad s), 5.32–5.33 (1H, m), 4.90 (1H, dd, J=3.2, 12.4 Hz), 4.60 (1H, dd, J=1.2, 12.4 Hz).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified by flash chromatography (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-fb1d4694eb7748e1a23d3e8329c61df9
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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