Isoamyl nitrate → HCID 19900853, compound

HRID 1029757Notes

Reaction equation

HRID 1029757 reaction equation
[CH3:1][C:2]1[S:3][C:4]([S:7][CH2:8]C(O)=O)=[CH:5][CH:6]=1.C([Li])CCC.[N+:17]([O-])([O:19]CCC(C)C)=[O:18]>CCCCCC>[CH3:1][C:2]1[S:3][C:4]([S:7][CH2:8][N+:17]([O-:19])=[O:18])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10985Isoamyl nitrateHCID 19900820HCID 19900820, compoundHCID 178418339Butyllithium

Product 1

HCID 19900853HCID 19900853, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The starting material was obtained using a similar procedure to that described for that in Example 9, but starting with 2-(2-methylthien-5-ylthio)acetic acid (described in Zh. Obsch. Khim. 1959, 29, 3631; 8.87 g), adding the butyllithium in hexane at -30° C. and the isoamyl nitrate at 0° C. The product 2-methyl-5-(nitromethylthio)thiophene, was obtained as an oil in 9% yield after column chromatography eluting with 10% ethyl acetate/hexane; NMR: 2.48 (s,3H), 5.38 (s,2H), 6.7 (m,1H), 7.1 (d,1H).

Workup

  1. customThe starting material was obtained
  2. customat 0° C

Sources & evidence

ORD record
ord-74b4eead94dd49ac926aed94c6f4517e
Source dataset
uspto-grants-1992_04
Patent number
US05102905

Reaction notes

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