Ethyl Acetate → HCID 59527523, compound

HRID 384449Notes

Reaction equation

HRID 384449 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](OCC)=[O:22])=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(OCC)(=O)C>C1COCC1>[O:7]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 59527136HCID 59527136, compound

Product 1

HCID 59527523HCID 59527523, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (418 mg) in anhydrous THF (25 mL) was added dropwise under ice-cooling a solution of ethyl 5-(2,3-dihydro-1,4-benzodioxin-6-yl)pentanoate (2.91 g) in anhydrous THF (10 mL) under nitrogen atmosphere. The mixture was stirred under ice-cooling for 30 minutes, and then a saturated aqueous sodium sulfate solution was added dropwise thereto, followed by stirring at room temperature for 1 hour. Ethyl acetate was added thereto, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=65/35) to obtain 5-(2,3-dihydro-1,4-benzodioxin-6-yl)pentan-1-ol (2.17 g).

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling for 30 minutes
  3. stirringby stirring at room temperature for 1 hour
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=65/35)

Sources & evidence

ORD record
ord-62675118631a40d889cd447212951d75
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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