Sodium Sulfate → HCID 19883160, compound

HRID 2291354Notes

Reaction equation

HRID 2291354 reaction equation
C(OCCC#C[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[CH:11][CH:10]=1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[O:15][C:12]1[CH:11]=[CH:10][CH:9]=[CH:14][C:13]=1/[CH:9]=[CH:10]/[CH2:11][CH2:12][OH:15]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 14988330HCID 14988330, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19883160HCID 19883160, compoundYield 193.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an anhydrous tetrahydrofuran solution containing 2.4 g of 4-[4-(2-tetrahydropyranyloxy)phenyl]-3-butynyl acetate was added 1 g of lithium aluminium hydride and the mixture was refluxed for 12 hours. After the reaction was completed, an aqueous solution saturated with sodium sulfate was slowly added to the reaction mixture, and the precipitation 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)-butenyl alcohol as in the form of colorless oily substance.

Workup

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

Sources & evidence

ORD record
ord-b7f31a6171014da9a4577f3d746b736a
Source dataset
uspto-grants-1989_01
Patent number
US04795814

Reaction notes

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