Sodium Bicarbonate → HCID 18351843, compound

HRID 430757Notes

Reaction equation

HRID 430757 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[C:16]2[O:15][CH:14]=[C:13]([CH2:17][C:18](OC)=[O:19])[C:12]=2[CH:11]=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])O.[Na+]>C1COCC1>[OH:19][CH2:18][CH2:17][C:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[C:16]=2[O:15][CH:14]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 54373590HCID 54373590, compound

Product 1

HCID 18351843HCID 18351843, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl (7-tetrahydropyranyloxybenzofuran-3-yl)acetate (355 mg) was dissolved in THF (4 ml) and the solution was cooled to 0° C. To this solution, lithium aluminum hydride (47 mg) was added and the solution was stirred at room temperature for 30 minutes. Saturated aqueous sodium hydrogen carbonate was added to the reaction solution and the solution was filtered through Celite. The filtrate was poured into water layer (30 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated saline, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=2/1) using silica gel to obtain the desired compound (289 mg, yield: 90%).

Workup

  1. filtrationthe solution was filtered through Celite
  2. additionThe filtrate was poured into water layer (30 ml)
  3. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  4. washwashed with saturated saline
  5. dry with materialby drying the resultant over sodium sulfate
  6. customAfter removing the sodium sulfate
  7. filtrationby filtration
  8. customthe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-c267fbb4cba44cffa94dd209818d697a
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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