HCID 15037140, compound → HCID 15037162, compound

HRID 273960Notes

Reaction equation

HRID 273960 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 (1.0M 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 10% aqueous HCl and the organics were extracted into ethyl ether. The combined fractins 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 10% aqueous HCl
  2. extractionthe organics were extracted into ethyl ether
  3. washThe combined fractins 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-4abf68f056114fef9f6cdf120bb8046b
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Reaction notes

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