Methanol → HCID 22509458, compound

HRID 984955Notes

Reaction equation

HRID 984955 reaction equation
C([O:3][C:4](=[O:31])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[C:16](/[C:18]2[CH:30]=[CH:29][C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][C:20]=3[CH:19]=2)\[CH3:17])=[CH:9][CH:8]=1)[CH3:6])C.CO>[OH-].[Na+].Cl.C(OCC)(=O)C>[CH:19]1[C:20]2[CH2:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]=2[CH:29]=[CH:30][C:18]=1/[C:16](/[CH3:17])=[CH:15]/[CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH:5]([CH3:6])[C:4]([OH:31])=[O:3])=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 69793194HCID 69793194, compound

Product 1

HCID 22509458HCID 22509458, compoundYield 73.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

(E)-{4-[3-(9H-Fluoren-2-yl)-but-2-enyloxy]-phenyl}-propionic acid ethyl ester (example 18) (220 mg, 0.53 mmol) was suspended in 1N NaOH (5.5 ml) and methanol (20 ml) and stirred for 24 h at room temperature. The mixture was diluted with 1N HCl (50 ml) and ethyl acetate (50 mL). The aqueous layer was separated and extracted with ethyl acetate (50 ml) The organic layers were combined, washed with brine, dried (MgSO4) and evaporated. The residue was recrystallised from boiling ethanol (20 ml) to give 150 mg (73%) of the title compound.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (50 ml) The organic layers
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was recrystallised

Sources & evidence

ORD record
ord-5b310cb693ac4ae4941aa6095d123592
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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