Potassium Sodium Tartrate → HCID 70405169, compound

HRID 1284463Notes

Reaction equation

HRID 1284463 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[C:7](/[C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][C:13](O)=[O:14])[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>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[C:7](/[C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:2]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 13285833HCID 13285833, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 70405169HCID 70405169, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(E)-7-(3-Pyridyl)-7-(2-thienyl)-6-heptenoic acid (0.4 g, 1.4 mmoles) was dissolved in dry tetrahydrofuran (20 ml) and lithium aluminum hydride (0.1 g, 2.6 mmoles) was added to the solution. The mixture was stirred at 50° C. for an hour, followed by addition of a saturated aqueous Rochelle salt solution (10 ml). The organic alyer was separated and the precipitate was washed with tetrahydrofuran (20 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 the eluent to give (E)-7-(3-pyridyl)-7-(2-thienyl)-6-hepten-1-ol (0.21 g, 52%) (Compound I-17).

Workup

  1. customThe organic alyer was separated
  2. washthe precipitate was washed with tetrahydrofuran (20 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-24f9edf318334859b7ab1aaf195342b2
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

Loading…