Diethyl Malonate → HCID 178470506, compound

HRID 2251968Notes

Reaction equation

HRID 2251968 reaction equation
[O-]CC.[Na+].[C:5]([O:13]CC)(=O)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[N:16]([CH2:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=1)=[N+:17]=[N-:18]>C(O)C>[CH2:10]([O:9][C:7]([C:6]1[N:18]=[N:17][N:16]([CH2:19][C:20]2[CH:21]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=2)[C:5]=1[OH:13])=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 441857431-(Azidomethyl)-3,5-bis(trifluoromethyl)benzene

Product 1

HCID 178470506HCID 178470506, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Combine a solution of sodium ethoxide (5.5 mL, 21 wt % in ethanol) and diethyl malonate (2.50 mL, 16.5 mmol) in ethanol (26 mL) with a solution of 1-azidomethyl-3,5-bis-trifluoromethyl-benzene (4.40 g, 16.3 mmol) in ethanol (6 mL) and heat to 80° C. After 7 hours, cool to RT. Concentrate mixture in vacuo and dissolve the viscous oil in H2O (20 mL). Add aqueous 1N HCl until solution reaches pH 2-3. Collect the white precipitate by filtration and dry under reduced pressure to give the title compound: MS (IS) 384.0 (M+H), MS (ES−) 382.1 (M−H); 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.92 (s, 2H), 5.41 (s, 2H), 4.15 (q, 2H, J=7.3), 1.22 (t, 3H, J=7.3).

Workup

  1. concentrationConcentrate mixture in vacuo
  2. dissolutiondissolve the viscous oil in H2O (20 mL)
  3. customCollect the white precipitate
  4. filtrationby filtration
  5. customdry under reduced pressure

Sources & evidence

ORD record
ord-4e0a18c15cfd4214872bba1f7fd6cba0
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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