Dimethylformamide → HCID 54300519, compound

HRID 344736Notes

Reaction equation

HRID 344736 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:3]=1[O:4][C:5]([CH3:12])([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:18][N:19](C)C=O>CN1C(=O)N(C)CCC1>[C:18]([C:2]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:3]=1[O:4][C:5]([CH3:12])([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:19]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 4508436HCID 4508436, compound

Product 1

HCID 54300519HCID 54300519, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
200 °C

Procedure

In a similar manner to Example 48(ii), but starting from ethyl 2-(2-chloro-5-methylphenoxy)-2-methylpropionate instead of ethyl 2-(2-bromo-4-methylphenoxy)-2-methylpropionate and using DMPU as solvent in place of dimethylformamide and heating for 18 hours at 200° C. there was obtained, after evaporation of the dichloromethane extracts a liquid. This was dissolved in ether (200 ml) and the solution washed with water (3×50 ml) to removed the DMPU, then dried (MgSO4) and evaporated. The residue was purified by MPLC, eluting with 10% v/v ethyl acetate in hexane to give ethyl 2-(2-cyano-5-methylphenoxy)-2-methylpropionate (38%) as a colourless oil; NMR (250 MHz, CDCl3): 1.24(3H,t J=7 Hz), 1.67(6H,s), 2.33(3H,s), 4.24(2H, q J=7 Hz), 6.60(1H,s), 6.84(1H,dm, J=8 Hz), 7.44(1H,d J=8 Hz); m/e 265 (M+NH4)+.

Workup

  1. customthere was obtained
  2. customafter evaporation of the dichloromethane
  3. dissolutionThis was dissolved in ether (200 ml)
  4. washthe solution washed with water (3×50 ml)
  5. customto removed the DMPU
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by MPLC
  9. washeluting with 10% v/v ethyl acetate in hexane

Sources & evidence

ORD record
ord-ee30e3d5f0864dfc90bf47cb609d9c82
Source dataset
uspto-grants-1991_10
Patent number
US05053415

Reaction notes

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