HCID 69655194, compound → HCID 21936925, compound

HRID 1241876Notes

Reaction equation

HRID 1241876 reaction equation
C([O:3][C:4]([CH:6]1[CH2:12][CH2:11][C:10]2[C:13]([O:17][CH3:18])=[CH:14][CH:15]=[CH:16][C:9]=2[C:8](=[O:19])[CH2:7]1)=[O:5])C>[OH-].[Na+].CCOCC>[CH3:18][O:17][C:13]1[C:10]2[CH2:11][CH2:12][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][C:8](=[O:19])[C:9]=2[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 69655194HCID 69655194, compound

Product 1

HCID 21936925HCID 21936925, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 0.7 g of (±)-1-methoxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-carboxylic acid ethyl ester (prepared as described in Bowman, Tetrahedron, 48, 4027, 1992) in 2 mL of 2N NaOH 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.

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-93e075eda2c94946a3583a0558b651c2
Source dataset
uspto-grants-2006_10
Patent number
US07115633B2

Reaction notes

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