(2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate → (Z)-4-Acetoxy-3-(4-(Methylsulfonyl)Phenyl)-2-Phenyl-2-Butenal

HRID 1458316Notes

Reaction equation

HRID 1458316 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)\[CH2:8][OH:9])(=[O:3])[CH3:2]>C(Cl)Cl.O=[Mn]=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)\[CH:8]=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 58787789(2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate

Product 1

HCID 86753445(Z)-4-Acetoxy-3-(4-(Methylsulfonyl)Phenyl)-2-Phenyl-2-ButenalYield 74.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of the acetate from Example 2 (215 mg) and MnO2 (1.2 g) in 30 mL of CH2Cl2 was stirred for 12 h at r.t., and then filtered through a pad of celite. The filtrate was concentrated to give 160 mg of the title compound as a yellow solid.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-15f6d70ffffc420eb899293d64cc0176
Source dataset
uspto-grants-1998_12
Patent number
US05849943

Reaction notes

Loading…