4-Nitrobenzaldehyde → HCID 54212014, compound

HRID 2254318Notes

Reaction equation

HRID 2254318 reaction equation
[Li+].CC([N-]C(C)C)C.[Br-].[CH3:10][C:11]1([CH:16]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH3:17])[O:15][CH2:14][CH2:13][O:12]1.[N+:37]([C:40]1[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=1)([O-:39])=[O:38].[NH4+].[Cl-]>C1COCC1.CS(C)=O>[N+:37]([C:40]1[CH:47]=[CH:46][C:43]([CH:44]=[CH:17][CH2:16][C:11]2([CH3:10])[O:12][CH2:13][CH2:14][O:15]2)=[CH:42][CH:41]=1)([O-:39])=[O:38]

Participants

7

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 86746412HCID 86746412, compound

Product 1

HCID 54212014HCID 54212014, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 62.8 mmol of LDA in 226.4 ml of THF, is added dropwise at 0° C. a solution of 28.8 g (62.2 mmol) of (2-methyl-dioxolane-2-yl-2-ethyl)triphenylphosphonium bromide in 60 ml of DMSO. After 1 h at 0° C., 7.8 g 51.6 mmol) of p-nitrobenzaldehyde dissolved in 40 ml of THF are added. The reaction medium is hydrolyzed with a NH4Cl saturated solution and is extracted with ethyl ether. The organic phase is dried over Na2SO4 and concentrated. After purification by flash chromatography (silica, eluent: heptane:70; ethyl acetate:30), the product is obtained with a 48% yield.

Workup

  1. additionare added
  2. extractionis extracted with ethyl ether
  3. dry with materialThe organic phase is dried over Na2SO4
  4. concentrationconcentrated
  5. customAfter purification by flash chromatography (silica, eluent: heptane:70; ethyl acetate:30)
  6. customthe product is obtained with a 48% yield

Sources & evidence

ORD record
ord-2360542e73ed41ed954b54a0cab1f037
Source dataset
uspto-grants-1993_08
Patent number
US05235063

Reaction notes

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