Methanol → HCID 59444543, compound

HRID 1513999Notes

Reaction equation

HRID 1513999 reaction equation
C[O:2][C:3]([CH:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=1)[C:6](OC)=[O:7])=O.[Li+].[BH4-].CO>C1COCC1>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:5]([CH2:3][OH:2])[CH2:6][OH:7])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 59444544HCID 59444544, compound

Product 1

HCID 59444543HCID 59444543, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 17 (1.19 g, 3.4 mmol) was dissolved in dry THF (50 mL). LiBH4 (0.44 g, 20.2 mmol) was added and the mixture was refluxed overnight. The mixture was allowed to cool to r.t. and MeOH (10 mL) was added. The reaction mixture was stirred for 30 min at r.t. The mixture was evaporated to dryness. Saturated aqueous NaHCO3 was added and the mixture was refluxed for one hour. The mixture was allowed to cool to r.t. and then filtered. The precipitate was washed with water and purified on silica gel (10% MeOH/CH2Cl2), yielding 0.60 g (67%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe mixture was evaporated to dryness
  3. additionSaturated aqueous NaHCO3 was added
  4. temperaturethe mixture was refluxed for one hour
  5. temperatureto cool to r.t.
  6. filtrationfiltered
  7. washThe precipitate was washed with water
  8. custompurified on silica gel (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3f26fbd145fd4ec5b1c44a690d5651d0
Source dataset
uspto-grants-2012_07
Patent number
US08221719B2

Reaction notes

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