Acetic Anhydride → (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate

HRID 1458315Notes

Reaction equation

HRID 1458315 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][OH:16])[CH2:12][OH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CCN(CC)CC.[CH3:30][C:31](OC(C)=O)=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:31]([O:13][CH2:12]/[C:11](/[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1)=[C:14](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)\[CH2:15][OH:16])(=[O:32])[CH3:30]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 542101292-[4-(Methanesulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-(methylsulfonyl)phenyl)-3-phenyl-2butene-1,4-diol (149 mg) and Et3N (0.2 mL) in 20 mL of CH2Cl2 was treated with Ac2O (0.05 mL) and DMAP (5 mg). After stirring for 10 min at r.t., the mixture was concentrated, and the residue was purified by flash chromatography eluted with 3:2 EtOAc/hexane to afford 40 mg of the title compound as a white solid along with 30 mg of its regioisomer as a syrup.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluted with 3:2 EtOAc/hexane

Sources & evidence

ORD record
ord-fbbecb40941b419db85b08ea2c4dd5a8
Source dataset
uspto-grants-1998_12
Patent number
US05849943

Reaction notes

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