HCID 86738185, compound → HCID 12802878, compound

HRID 1660555Notes

Reaction equation

HRID 1660555 reaction equation
[Cl:1][C:2]1[C:3](/[CH:16]=[CH:17]/[C@H:18]2[O:23][C:22](=[O:24])[CH2:21][C@@H:20]([OH:25])[CH2:19]2)=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1>CCOCC>[Cl:1][C:2]1[C:3](/[CH:16]=[CH:17]/[C@@H:18]2[O:23][C:22](=[O:24])[CH2:21][C@@H:20]([OH:25])[CH2:19]2)=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 1

HCID 86738185HCID 86738185, compound

Product 1

HCID 12802878HCID 12802878, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of cis-(E)-6-[2-(3,5-dichloro-4'-fluoro-2-[1,1'-biphenyl]yl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (7.6 g, 20 mmole) and mercuric chloride (6 g, 22 mmole) was stirred at gentle reflux in H2O--acetonitrile (1:5; V:V; 120 ml) under N2 for 68 hours. The cooled reaction mixture was then diluted with Et2O (1 liter), washed with H2O (3×500 ml), and brine, dried (MgSO4), filtered and evaporated in vacuo to provide the crude title compound (7 g) as a pale amber gum (56% cis and 44% trans by HPLC).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with H2O (3×500 ml), and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-f9af797072a04d1da2bf16f1b686dc26
Source dataset
uspto-grants-1981_12
Patent number
US04308378

Reaction notes

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