Sulfuric Acid → (E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhex-3-enoate

HRID 563414Notes

Reaction equation

HRID 563414 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17](O)([CH2:25][CH:26]([CH3:28])[CH3:27])[C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.OS(O)(=O)=O>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](/[C:17](=[CH:25]\[CH:26]([CH3:28])[CH3:27])/[C:18]([CH3:23])([CH3:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 59252801methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-hydroxy-2,2,5-trimethylhexanoate

Product 1

HCID 67006057(E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhex-3-enoateYield 82.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-hydroxy-2,2,5-trimethylhexanoate (280 mg, 0.7 mmol) was dissolved in 10 mL MeOH and 5 mL H2SO4 and heated at 90° C. for 12 h. After 12 h, diluted with water and extracted with EtOAc×3. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by SiO2 chromatography eluting with 1:9 EtOAc/hexane. Obtained 220 mg (82% yield) of (E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,5-trimethylhex-3-enoate. MS found: (M+H)+=381.

Workup

  1. extractionextracted with EtOAc×3
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography
  6. washeluting with 1:9 EtOAc/hexane

Sources & evidence

ORD record
ord-baf65a778bc749caad5617647e9006b5
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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