Sodium Sulfate → HCID 54315455, compound

HRID 2260659Notes

Reaction equation

HRID 2260659 reaction equation
[C:1]1([C:7]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:8]2[C:12]([CH:13]=[C:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[CH2:18][S:17][C:16]4[CH:25]=[C:26]([C:29](OC)=[O:30])[CH:27]=[CH:28][C:15]3=4)=[N:11][N:10]=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC.C1COCC1>[OH:30][CH2:29][C:26]1[CH:27]=[CH:28][C:15]2[C:14](=[CH:13][C:12]3[N:8]([C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:9]=[N:10][N:11]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][S:17][C:16]=2[CH:25]=1

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 70286408HCID 70286408, compound

Product 1

HCID 54315455HCID 54315455, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 21-b (3.8 g, 6.4 mmol) was dissolved in a mixture of 80 ml of ether and 40 ml of THF, and 250 mg (6.6 mmol) of lithium aluminium hydride was added to the solution under ice cooling, followed by stirring at room temperature for one hour and a half. To the mixture was added 1 ml of a saturated aqueous solution of sodium sulfate and insoluble matters were filtered off. The filtrate was diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (5/1)] to give the E form (21-c-E; 40%) and the Z form (21-c-Z; 41%) as colorless oily substances.

Workup

  1. additionwas added to the solution under ice cooling
  2. filtrationwere filtered off
  3. additionThe filtrate was diluted with ethyl acetate
  4. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (5/1)]
  8. customto give the E form (21-c-E; 40%)

Sources & evidence

ORD record
ord-c184bbf40ea14c03bf1c45b07fa974dc
Source dataset
uspto-grants-1995_12
Patent number
US05478840

Reaction notes

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