Sodium Hydroxide → HCID 22500388, compound

HRID 1815447Notes

Reaction equation

HRID 1815447 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:10]=1[S:7]([CH2:6][CH2:5][CH2:4][CH2:3][OH:2])(=[O:9])=[O:8]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 43516938HCID 43516938, compound

Product 1

HCID 22500388HCID 22500388, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of the product of step b (1.00 g, 3.27 mmol) in THF (10 ml) was added dropwise a solution of lithium aluminium hydride (1M, THF, 3.50 ml, 3.50 mmol) and the mixture was stirred at this temperature for 3 h. The reaction mixture was treated sequentially with water (0.14 ml), aqueous sodium hydroxide (2M, 0.14 ml) and water (0.42 ml) and allowed to warm to ambient temperature. Sodium sulfate was added and the resultant suspension filtered through a pad of celite and the filter-cake washed with further ethyl acetate (150 ml). The filtrate was evaporated at reduced pressure and the residue purified by flash column chromatography (3:1 ethyl acetate:hexane) to afford the title compound (524 mg, 61%). 1H NMR 8.50 (1H, s), 8.04-7.86 (4H, m), 7.72-7.63 (2H, m), 3.66-3.62 (2H, m), 3.27-3.21 (2H, m), 1.91-1.83 (2H, m), 1.71-1.65 (2H, m), 1.56 (1H, br s).

Workup

  1. filtrationthe resultant suspension filtered through a pad of celite
  2. washthe filter-cake washed with further ethyl acetate (150 ml)
  3. customThe filtrate was evaporated at reduced pressure
  4. customthe residue purified by flash column chromatography (3:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-030af5dccd174921afb423b5fc72c0de
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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