Sodium Hydroxide → HCID 22273758, compound

HRID 1064376Notes

Reaction equation

HRID 1064376 reaction equation
[CH:1]1[C:6]2[CH2:7][CH2:8][CH:9]([C:13]([O:15]CC)=[O:14])[CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CCOCC>[CH:1]1[C:6]2[CH2:7][CH2:8][CH:9]([C:13]([OH:15])=[O:14])[CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10922397HCID 10922397, compound

Product 1

HCID 22273758HCID 22273758, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 0.7 g (3 mmol) of ethyl (±)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one-7-carboxylate (prepared as described in Bowman, Tetrahedron, 48, 4027, 1992) in 2 mL of 2N NaOH (4 mmol) was refluxed for 2 h, then cooled and extracted with Et2O. The aqueous layer was brought to acidic pH with 10% HCl, the precipitate formed was redissolved in Et2O and the organic phase was washed with water and dried. The solvent was removed in vacuo and the resulting residue was purified by flash chromatography, eluting with a mixture CH2Cl2/MeOH 9:1 respectively, yielding 0.41 g of the title compound. m.p.=134-135° C.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturecooled
  3. extractionextracted with Et2O
  4. customthe precipitate formed
  5. washthe organic phase was washed with water
  6. customdried
  7. customThe solvent was removed in vacuo
  8. customthe resulting residue was purified by flash chromatography
  9. washeluting with a mixture CH2Cl2/MeOH 9:1 respectively

Sources & evidence

ORD record
ord-21df31a6e8a14b64a2a858f764705180
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

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