Sodium Hydroxide → HCID 9861952, compound

HRID 844358Notes

Reaction equation

HRID 844358 reaction equation
C([O:3][C:4](=[O:26])[C:5](=[O:25])[CH2:6][C:7](=[O:24])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)[CH:9]=1)C.[OH-].[Na+]>CO.O>[O:25]=[C:5]([CH2:6][C:7](=[O:24])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)[CH:9]=1)[C:4]([OH:26])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 18736271HCID 18736271, compound

Product 1

HCID 9861952HCID 9861952, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Isomer A: 2,4-dioxo-4-[3-(1,2,3,4-tetrahydronaphthalen-1-yl)-phenyl]butyric acid ethyl ester (isomer A from above) was dissolved in 2 mLs methanol, and to it was added 1 mL of a 1M solution of sodium hydroxide in water. After stirring for 4 hr, the reaction was poured into 5 mL sodium hydroxide and extracted three times with diethyl ether. The aqueous layer was then acidified via the addition of excess 10% citric acid and extracted three times with ethyl acetate. The ethyl acetate extracts were combined and washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the solvent removed in vacuo. The residue was triturated in 3:1 hexane/diethyl ether, filtered and the solvent removed in vacuo to yield the title compound as a yellow solid. 1H NMR (CDCl3) δ1.72-1.91(3H,m), 2.20(1H,m), 2.80-3.00(2H,m), 4.22(1H, t, J=7.14Hz), 6.77(1H, d, J=7.69 Hz), 7.03(1H, t, J=7.42Hz), 7.11-7.19(3H,m), 7.31(1H, d, J=7.69Hz), 7.41(1H, t, J=7.69Hz), 7.80(1H,s), 7.84(1H, d, J=7.88Hz).

Workup

  1. extractionextracted three times with diethyl ether
  2. additionThe aqueous layer was then acidified via the addition of excess 10% citric acid
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was triturated in 3:1 hexane/diethyl ether
  9. filtrationfiltered
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cf01586d80964ecd80cadd34e7c84d66
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

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