Diethyl Malonate → HCID 178470506, compound

HRID 349250Notes

Reaction equation

HRID 349250 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 h, cool to RT and concentrate the mixture in vacuo. Dissolve the viscous oil in H2O (20 mL) and add aqueous 1N HCl until the solution reaches pH 2–3. Collect the white precipitate by filtration and dry under reduced pressure to give the title compound. MS (ES) 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 Hz), 1.22 (t, 3H, J=7.3 Hz).

Workup

  1. concentrationconcentrate the mixture in vacuo
  2. dissolutionDissolve the viscous oil in H2O (20 mL)
  3. additionadd aqueous 1N HCl until the solution
  4. customCollect the white precipitate
  5. filtrationby filtration
  6. customdry under reduced pressure

Sources & evidence

ORD record
ord-d5da0ebea938457f93a98c1b1cdf2c0a
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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