Sodium Hydroxide → HCID 69272289, compound

HRID 747384Notes

Reaction equation

HRID 747384 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[C:10]([N+:12]([O-])=O)[CH3:11])[C:6]([O:15][CH3:16])=[CH:5][C:4]=1[CH2:17][CH2:18][O:19][CH2:20][O:21][CH3:22].[H-].[H-].[H-].[H-].[Li+].[Al+3].[Li].[H-].[OH-].[Na+]>C1COCC1.C(OCC)C.O>[CH3:16][O:15][C:6]1[CH:5]=[C:4]([CH2:17][CH2:18][O:19][CH2:20][O:21][CH3:22])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[CH2:9][CH:10]([NH2:12])[CH3:11]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 3028194LithiumHCID 21226445Aluminium lithium hydrideHCID 69011582HCID 69011582, compound

Product 1

HCID 69272289HCID 69272289, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold solution (ice bath) of 1,4-Dimethoxy-2-(2-methoxymethoxy-ethyl)-5-(2-nitropropenyl)-benzene (0.83 g, 2.67 mmol) in 10 mL of dry THF was added dropwise a solution of 1 M LAH in THF (10.67 mL, 10.67 mmol). The reaction mixture was allowed to warm to room temperature and stir overnight. The excess lithium aluninLm hydride was decomposed by careful addition of 0.4 mL of water, 0.4 mL of 15% NaOH, and 1.2 mL of water. The reaction mixture was diluted with 50 mL of ethyl ether. The heterogeneous solution was stirred for 5 min and then filtered and the precipitate was washed with ethyl ether. The combined filtrates were dried (MgSO4) and concentrated under reduced pressure to give a solid. MS (m/z) 284 (M+1)+. 1HNMR(CDCl3): δ ppm 1.03 (d, 3H), 2.46 (m, 1H), 2.65 (m, 2H), 2.83 (m, 2H), 3.25 (m, 3H), 3.65-3.75 (m, 9H), 4.56 (s, 2H), 6.59 (s, 1H), 6.66 (s, 1H).

Workup

  1. stirringThe heterogeneous solution was stirred for 5 min
  2. filtrationfiltered
  3. washthe precipitate was washed with ethyl ether
  4. dry with materialThe combined filtrates were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a solid

Sources & evidence

ORD record
ord-cf06dc12f037427892401a8696341b56
Source dataset
uspto-grants-2008_07
Patent number
US07396856B2

Reaction notes

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