Water → HCID 21460407, compound

HRID 1941218Notes

Reaction equation

HRID 1941218 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]([CH3:17])([CH3:16])[C:14](=O)[NH:13][C:12]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]([CH3:16])([CH3:17])[CH2:14][NH:13][C:12]1=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21460389HCID 21460389, compound

Product 1

HCID 21460407HCID 21460407, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9a (28 g) in THF (250 ml) was added to a suspension of LiAlH4 (8 g) in THF (250 ml) at 20°-25° C. After stirring at room temperature for 1 h, the mixture was cooled to 0° C., water (10 ml) and aqueous NaOH (10 ml) were added, the inorganic salts were filtered and the solvents were evaporated in vacuo. The remaining oil was purified by column chromatography on silica gel (ethyl acetate) yielding 9b as an oil: 10 g.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. filtrationthe inorganic salts were filtered
  3. customthe solvents were evaporated in vacuo
  4. customThe remaining oil was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-180901c99f9e4ba4ad2a187ceb62ad02
Source dataset
uspto-grants-1997_12
Patent number
US05703087

Reaction notes

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