HCID 15037140, compound → HCID 15037162, compound

HRID 488245Notes

Reaction equation

HRID 488245 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[O:12][C:11]([Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:9]=1[CH:20]=[O:21]>O1CCCC1>[CH3:7][C:8]1[O:12][C:11]([Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:9]=1[CH2:20][OH:21]

Participants

4

Reactant 2

HCID 15037140HCID 15037140, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15037162HCID 15037162, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.0 M solution in hexane, 0.51 ml, 0.51 mmol) was added dropwise to a solution of 5-methyl-2-triethylsilyl-4-furaldehyde (230 mg, 1.03 mmol) in tetrahydrofuran (15 ml) at 0 degrees under argon. The stirring solution was allowed to warm to room temperature gradually over 1/2 hour. The reaction was quenched with I0% aqueous HCl and the organics were extracted into ethyl ether. The combined fractions were washed with H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by filtration through silica using 10% ethyl ether/hexanes to give the title compound.

Workup

  1. customThe reaction was quenched with I0% aqueous HCl
  2. extractionthe organics were extracted into ethyl ether
  3. washThe combined fractions were washed with H2O and brine
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil which
  7. filtrationwas purified by filtration through silica using 10% ethyl ether/hexanes

Sources & evidence

ORD record
ord-3dbc22fbe24d473095638a84451b8bec
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Reaction notes

Loading…