Pyridinium chloride → Methanone, [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]phenyl-

HRID 1956805Notes

Reaction equation

HRID 1956805 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18]C)[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:21])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 22753379[6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophen-3-yl](phenyl)methanone

Product 1

HCID 9841167Methanone, [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]phenyl-

Procedure

2.5 g (6.7 mmol) of [2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][phenyl] methanone mixed with 10 g of pyridine hydrochloride and fused at 220° C. for 1.5 hours. The reaction mixture was poured into ice-water and mixture extracted with 500 mL of EtOAc. The EtOAc layer was separated, washed with brine, dried with MgSO4, and evaporated to a yellow oil. The product was crystallized from MeOH--HOH. This yielded 2.1 g of the title compound as yellow crystalline solid.

Workup

  1. extractionextracted with 500 mL of EtOAc
  2. customThe EtOAc layer was separated
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. customevaporated to a yellow oil
  6. customThe product was crystallized from MeOH

Sources & evidence

ORD record
ord-675beeed35db40ae8578be37f00942f0
Source dataset
uspto-grants-1998_07
Patent number
US05780648

Reaction notes

Loading…