Tetrahydrofuran → HCID 54394866, compound

HRID 1927269Notes

Reaction equation

HRID 1927269 reaction equation
C1COCC1.[O:6]([C:13]1[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[O:6]([C:13]1[S:17][C:16]([CH2:18][OH:19])=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 13679816HCID 13679816, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54394866HCID 54394866, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of THF (60 mL) and 5-phenoxy-thiophene-2-carbaldehyde (2.8 g) was added LAH (390 mg) at 0° C., which was stirred for 10 minutes at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The solvent was evaporated under a reduced pressure and the organic layer was purified by NH silica gel chromatography (ethyl acetate), and then purified by silica gel chromatography (hexane:ethyl acetate=4:1, then 2:1) to obtain the titled compound (2.0 g).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. customThe solvent was evaporated under a reduced pressure
  3. customthe organic layer was purified by NH silica gel chromatography (ethyl acetate)
  4. custompurified by silica gel chromatography (hexane

Sources & evidence

ORD record
ord-69c528d31f404ecf990632628bb9a297
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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