Sodium Hydroxide → HCID 12094927, compound

HRID 1767760Notes

Reaction equation

HRID 1767760 reaction equation
[C:1]1([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9](OCC)=[O:10])[CH2:5][CH2:4][CH2:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>CCOCC>[C:1]1([C:6]2[CH:7]=[C:8]([CH2:9][OH:10])[CH:14]=[CH:15][CH:16]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12094926Ethyl 3-cyclopenten-1-ylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12094927HCID 12094927, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 3-cyclopent-1-ylbenzoate (4a) (2.5 g, 12 mmol) in ether (25 ml) is added dropwise to a suspension at 0° C. of LiAlH4 (0.57 g, 15 mmol) in ethyl ether (30 ml). The mixture is stirred overnight at room temperature. The reaction mixture is cooled to 0° C. and then 4.1 ml of a 10% aqueous sodium hydroxide solution are added dropwise. The white precipitate formed is filtered under vacuum, the solid washed with ether and then the filtrate concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 90/10). The title product (1.35 g) is obtained in the form of a colorless oil.

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. customThe white precipitate formed
  3. filtrationis filtered under vacuum
  4. washthe solid washed with ether
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 90/10)

Sources & evidence

ORD record
ord-0e158c4ecc3644c4ae04879f47bfd1f0
Source dataset
uspto-grants-2007_06
Patent number
US07235568B2

Reaction notes

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