Potassium Sodium Tartrate → HCID 13417327, compound

HRID 1284462Notes

Reaction equation

HRID 1284462 reaction equation
[C:1]1(/[C:7](/[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][C:13](OCC)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[C:1]1(/[C:7](/[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 13417304HCID 13417304, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13417327HCID 13417327, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl (E)-7-phenyl-7-(3-pyridyl)-6-heptenoate (1.5 g, 4.8 mmoles) was dissolved in dry tetrahydrofuran (30 ml) and ice-cooled. Lithium aluminum hydride (0.5 g) was gradually added to the solution. The mixture was stirred at 0° C. for 30 minutes and a saturated aqueous Rochelle salt solution was added to precipiate the inorganic substance. The organic layer was separated and the precipitate was washed with tetrahydrofuran (30 ml). The tetrahydrofuran solutions were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate as eluent to give (E)-7-phenyl-7-(3-pyridyl)-6-hepten-1-ol (1.2 g, 94%) (Compound Id-14) as an oil.

Workup

  1. temperatureice-cooled
  2. customThe organic layer was separated
  3. washthe precipitate was washed with tetrahydrofuran (30 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf0b18a9b5914d32bf9e0602d983000d
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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