Methanol → HCID 59994483, compound

HRID 2383304Notes

Reaction equation

HRID 2383304 reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.[CH3:8][C:9]1[C:14](/[CH:15]=[CH:16]/[N+:17]([O-])=O)=[CH:13][CH:12]=[CH:11][C:10]=1[O:20][CH3:21].CO>C1COCC1>[CH3:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][CH:12]=[CH:13][C:14]=1[CH2:15][CH2:16][NH2:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 59370485HCID 59370485, compound

Product 1

HCID 59994483HCID 59994483, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To lithium borohydride (2M in THF; 2.00 ml; 4.00 mmol) was added dropwise over 0.5 min chlorotrimethylsilane (1.02 ml; 8.00 mmol). A precipitate was formed and after ca. 3 min, 2-methyl-1-(methyloxy)-3-[(E)-2-nitroethenyl]benzene (Preparation 9, 193 mg; 1.00 mmol) in THF (4 ml) was added dropwise via syringe over 5 min, making sure that the temperature remained at ca. 25° C. (using a water cold bath). The solution was stirred at room temperature overnight. The mixture was cooled with an ice bath, methanol was added slowly, and the solvent removed. The residue was partitioned between 25% aqueous sodium hydroxide and dichloromethane (3 extractions), and the solvent evaporated. Purification of the residue by solid phase extraction (SCX column) gave the title compound (80 mg).

Workup

  1. customA precipitate was formed and after ca. 3 min
  2. customremained at ca. 25° C.
  3. temperatureThe mixture was cooled with an ice bath
  4. customthe solvent removed
  5. customThe residue was partitioned between 25% aqueous sodium hydroxide and dichloromethane (3 extractions)
  6. customthe solvent evaporated
  7. customPurification of the residue
  8. extractionby solid phase extraction (SCX column)

Sources & evidence

ORD record
ord-be05f3e4c8474bb68e4ee63885ed70f3
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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