Sodium hydride → HCID 68488235, compound

HRID 1875053Notes

Reaction equation

HRID 1875053 reaction equation
[H-].[Na+].[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:20]=1[F:35]>C1COCC1>[F:35][C:20]1[C:21]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[CH:4]([C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68324Di-tert-butyl malonateHCID 68487133HCID 68487133, compound

Product 1

HCID 68488235HCID 68488235, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% oil dispersion) (3.75 g, 94 mmol) was added in portions to a solution of di-t-butyl malonate (10.49 ml, 46.9 mmol) in THF (200 mL). After gas evolution subsided, a solution of 1,2-difluoro-4-nitro-3-(phenyloxy)benzene (10.70 g, 42.6 mmol) in THF (100 mL) was added. The mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into ice and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated. Chromatography of the residue (ethyl acetate:hexanes) gave the desires product (2.38 g, 12.5%) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 7.81 (dd, 1H), 7.53 (dd, 1H), 7.27-7.35 (m, 2H), 7.09 (t, 1H), 6.93 (d, 2H), 4.80 (s, 1H), 1.48 (s, 18H). ES MS: m/z 470 (M+23).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-046ef9179d59401f8a922afbe54cb9b6
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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