2-Methyl-2-butene → (Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acid

HRID 1458317Notes

Reaction equation

HRID 1458317 reaction equation
[C:1]([O:4][CH2:5]/[C:6](/[C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[C:7](/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)\[CH:8]=[O:9])(=[O:3])[CH3:2].CC(=CC)C.[O-:31]Cl=O.[Na+]>CC(O)(C)C.O>[C:1]([O:4][CH2:5]/[C:6](/[C:16]1[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1)=[C:7](/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)\[C:8]([OH:31])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86753445(Z)-4-Acetoxy-3-(4-(Methylsulfonyl)Phenyl)-2-Phenyl-2-Butenal

Product 1

HCID 11617716(Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acidYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of the aldehyde from Example 3 (160 mg) and 2-methyl-2-butene (6 mL) in 2-methyl-2-propanol (35 mL) was added a solution of NaClO2 (1 g) and NaH2PO4 (1 g) in 10 mL of H2O. The mixture was stirred for 2 h at r.t., and concentrated. The residue was then taken into 50 mL of pH 7 buffer solution (1M) and extracted with EtOAc (50 mL). The extract was dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 3:1 EtOAc/hexane containing 1% HOAc to give 150 mg of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 3:1 EtOAc/hexane containing 1% HOAc

Sources & evidence

ORD record
ord-30fb426d7eb843a6b2e46158176bb47e
Source dataset
uspto-grants-1998_12
Patent number
US05849943

Reaction notes

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