Methanol → HCID 10156011, compound

HRID 984954Notes

Reaction equation

HRID 984954 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[C:15](/[C:17]2[CH:29]=[CH:28][C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][C:19]=3[CH:18]=2)\[CH3:16])=[CH:8][CH:7]=1)C.CO>[OH-].[Na+]>[CH:18]1[C:19]2[CH2:20][C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]=2[CH:28]=[CH:29][C:17]=1/[C:15](/[CH3:16])=[CH:14]/[CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:30])=[O:3])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 69795706HCID 69795706, compound

Product 1

HCID 10156011HCID 10156011, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

(E)-{4-[3-(9H-Fluoren-2-yl)-but-2-enyloxy]-phenyl}-acetic acid ethyl ester (example 16) (193 mg, 0.5 mmol) was suspended in 1N NaOH (5.0 mL) and methanol (5 mL) and stirred for 16 h at room temperature. A 2nd portion and 1N NaOH was added and stirring continued for 24 h. The mixture was concentrated to 10 mL volume then diluted with 1N HCl (50 mL) and ethyl acetate (150 mL). The aqueous layer was separated and extracted with ethyl acetate (50 mL) The organic layers were combined, dried (NaSO4) and evaporated. The residue was recrystallised from ethyl acetate (50 ml) to give 140 mg (75%) of the title compound as an pale yellow powder.

Workup

  1. concentrationThe mixture was concentrated to 10 mL volume
  2. additionthen diluted with 1N HCl (50 mL) and ethyl acetate (150 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (50 mL) The organic layers
  5. dry with materialdried (NaSO4)
  6. customevaporated
  7. customThe residue was recrystallised from ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-97c46fed36e0496b89f880fc4cf7a8a3
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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