Potassium Hydroxide → HCID 67198714, compound

HRID 1860295Notes

Reaction equation

HRID 1860295 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([O:28]C)=[O:27])=[CH:20][CH:19]=2)=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH3:11])=[CH:4][CH:3]=1.[OH-].[K+]>CO.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:19]=[CH:20][C:21]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])=[CH:22][CH:23]=2)=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69858985HCID 69858985, compound

Product 1

HCID 67198714HCID 67198714, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester (5) (300 mg, 0.78 mmol) in methanol (25 mL) and THF (8 mL) was added 1N KOH (12 mL, 12 mmol). After stirring overnight the solvent was partially removed under reduced pressure, the mixture was acidified with 1N HCl, and was extracted with EtOAc. The combined organic layers were washed with brine and were dried (MgSO4). The solvent was removed under reduced pressure and the residue was chromatographed (silica gel, 5% methanol/CH2Cl2) to give the acid (6) as a white solid (270 mg, 93%): 1 H NMR (CDCl3) δ 7.60 (d, J=15.8 Hz, 1 H), 7.13 (m, 11 H), 6.87 (d, J=8.5 Hz, 2 H), 6.28 (d, J=15.8 Hz, 1 H), 2.47 (q, J=7.3 Hz, 2 H), 0.93 (t, J=7.3 Hz, 3 H); APcI m/z: 414 (M+H+CH3CN+, 100%).

Workup

  1. customwas partially removed under reduced pressure
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialwere dried (MgSO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was chromatographed (silica gel, 5% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-bca8a58fdf7340ab9aa2d54e568bbbab
Source dataset
uspto-grants-2003_03
Patent number
US06528681B2

Reaction notes

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