Sodium Dithionite → HCID 19369865, compound

HRID 849037Notes

Reaction equation

HRID 849037 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[C:9]([O:33][CH3:34])=[C:10]([O:31][CH3:32])[C:11]2[O:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=O)([CH3:16])[CH2:13][C:12]=2[C:29]=1[CH3:30].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1>[OH:7][C:8]1[C:9]([O:33][CH3:34])=[C:10]([O:31][CH3:32])[C:11]2[O:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)([CH3:16])[CH2:13][C:12]=2[C:29]=1[CH3:30]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 19369856HCID 19369856, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19369865HCID 19369865, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.50 g) was added to a solution (30 ml) of 4-[5-(2,3-dihydro-5-hydroxy-6,7-dimethoxy-2,4-dimethylbenzofuran-2-yl)pentanoyl]morpholine (2.6 g) in tetrahydrofuran, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into an aqueous sodium hydrosulfite solution, and the insoluble materials were filtered off. The filtrate was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol =95:5) to obtain the title compound (2.2 g, 88%) as an oil.

Workup

  1. filtrationthe insoluble materials were filtered off
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:methanol =95:5)

Sources & evidence

ORD record
ord-07bc86da621a4509873119fb60f68a3d
Source dataset
uspto-grants-2000_01
Patent number
US06011046

Reaction notes

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