Isoamyl Nitrite → HCID 86759068, compound

HRID 1358155Notes

Reaction equation

HRID 1358155 reaction equation
C[O-].[Na+].[N:4](OCCC(C)C)=[O:5].[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:24])[CH2:21][CH2:22][CH3:23])=[CH:16][CH:15]=1>CO.O1CCCC1>[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:24])[C:21](=[N:4][OH:5])[CH2:22][CH3:23])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 10942334Sodium MethoxideHCID 18183644HCID 18183644, compound

Product 1

HCID 86759068HCID 86759068, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.0 g (0.206 mol) of sodium methoxide is suspended in 130 ml of methanol. Then isoamyl nitrite (27 ml, 0.206 mol) and 25 g (0.129 mol) of 1-(4-Methylsulfanyl-phenyl)-butan-1-one dissolved in 70 ml of tetrahydrofuran (THF) are added and the reaction solution is stirred at room temperature for 1.5 days. After concentrating, water and acetic acid are added to neutralise. The crude product is extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (15:85) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ[ppm]: 1.14 (t, 3H), 2.52 (s, 3H), 2.72 (q, 2H), 7.25 (d, 2H), 7.89 (d, 2H), 8.01 (s, 1H).

Workup

  1. additionare added
  2. concentrationAfter concentrating
  3. additionwater and acetic acid are added
  4. extractionThe crude product is extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (15:85) as an eluent

Sources & evidence

ORD record
ord-5b0f4e6c4cc74a878aaa9d4939dae047
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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