HCID 15037140, compound → HCID 15037162, compound

HRID 2081342Notes

Reaction equation

HRID 2081342 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, compound2×HCID 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 (Compound 38, 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 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 10% 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-4230c37a42284776a968a8d0b0880d6e
Source dataset
uspto-grants-1993_02
Patent number
US05183906

Reaction notes

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