Water → HCID 117396777, compound

HRID 523991Notes

Reaction equation

HRID 523991 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[CH:22][N+:23]([O-])=O)[C:16]=1[O:26][CH3:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([O:14][C:15]1[C:16]([O:26][CH3:27])=[C:17]([CH2:21][CH2:22][NH2:23])[CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 561829AGN-PC-0JSX8CHCID 21226445Aluminium lithium hydride

Product 1

HCID 117396777HCID 117396777, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 13.6 mL (32.6 mmol) lithium aluminum hydride solution (2.4 M in THF) are added dropwise 4.20 g (14.8 mmol) 1-benzyloxy-2-methoxy-3-(2-nitro-vinyl)-benzene (example X) in 20 mL THF at 0° C. After stirring at 0° C. for 2 h the reaction mixture is quenched by the addition of 0.59 mL (33 mmol) water, 8.20 mL (32.6 mmol) aq. NaOH solution (c=4 mol/L) and 1.80 mL (97.9 mmol) water. The resulting mixture is stirred for 20 min and filtered over celite/Na2SO4. The filtrate is concentrated by evaporation and the residue is purified by HPLC (ACN/H2O/NH4OH). After HPLC, ACN is removed in vacuo and the aq. layer is extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo.

Workup

  1. stirringThe resulting mixture is stirred for 20 min
  2. filtrationfiltered over celite/Na2SO4
  3. concentrationThe filtrate is concentrated by evaporation
  4. customthe residue is purified by HPLC (ACN/H2O/NH4OH)
  5. customAfter HPLC, ACN is removed in vacuo
  6. extractionthe aq. layer is extracted with EtOAc
  7. dry with materialThe organic layer is dried over MgSO4
  8. filtrationfiltered
  9. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5fbfd5bc858c4f79a1faf245f406d642
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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