Sodium Sulfate → HCID 19883160, compound

HRID 1087141Notes

Reaction equation

HRID 1087141 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11](C#CCCCC([O-])=O)=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1/[CH:5]=[CH:4]/[CH2:3][CH2:2][OH:1]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 19883149HCID 19883149, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19883160HCID 19883160, compoundYield 192.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an anhydrous tetrahydrofuran solution containing 2.4 g of 4-[4-(2-tetrahydropyranyloxy)phenyl]-3-butynylacetate was added 1 g of lithium aluminium hydride and the mixture was refluxed for 12 hours. After the reaction was finished, a saturated sodium sulfate aqueous solution was slowly added to the reaction mixture, and the precipitates formed were removed by filtration, then the filtrate was dried with anhydrous sodium sulfate, and concentrated to dryness. The residue thus obtained was purified by means of a silica gel column chromatography to yield 2 g of 4-[(2-tetrahydropyranyloxy)phenyl]-3(E)-butenylalcohol as in the form of colorless oily substance.

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. customthe precipitates formed
  3. customwere removed by filtration
  4. dry with materialthe filtrate was dried with anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue thus obtained
  7. customwas purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-503e78757e35428c9f1b65960e8b46f4
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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