Reaktion #981384

ord-1c9ffca1b4cc4110bc7077c60b236f4f

Reaktionsgleichung

CS(=O)[O-].[Na+]
methanesulfinic acid sodium salt
COC(=O)c1ccc2c(c1)C(O)c1ccccc1CO2
methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylate
O=S(Cl)Cl
thionyl chloride
CN(C)C=O
N,N-dimethylformamide
→
COC(=O)c1ccc2c(c1)C(S(C)(=O)=O)c1ccccc1CO2
title product
Ausbeute 68.6%
COC(=O)c1ccc2c(c1)C(S(C)(=O)=O)c1ccccc1CO2
Methyl 6,11-Dihydro-11-methylsulfonyldibenz[b,e]oxepin-2-carboxylate
Ausbeute 68.6%

Edukte

CS(=O)[O-].[Na+]
methanesulfinic acid sodium salt
COC(=O)c1ccc2c(c1)C(O)c1ccccc1CO2
methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylate
O=S(Cl)Cl
thionyl chloride
CN(C)C=O
N,N-dimethylformamide

Reagenzien

Keine

Lösungsmittel

O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturReflux 1.4 gm
  2. 2
    SonstigeStrip away excess thionyl chloride by evaporation
  3. 3
    workup.DISSOLUTIONdissolve the chloro intermediate
  4. 4
    Sonstigeso produced in 14 cc
  5. 5
    workup.ADDITIONAdd 582 mg
  6. 6
    Sonstigeseparate the solids
  7. 7
    Filtrationby filtration
  8. 8
    SonstigeCrystallize from 15 cc

Vorschrift

Reflux 1.4 gm. of methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylate in 6 cc. of thionyl chloride for 10 minutes. Strip away excess thionyl chloride by evaporation and dissolve the chloro intermediate so produced in 14 cc. of N,N-dimethylformamide. Add 582 mg. of methanesulfinic acid sodium salt (10% excess). Stir at room temperature for 5 days. Dilute with water and separate the solids by filtration. Crystallize from 15 cc. of benzene to obtain the title product (yield 1.18 gm. 68.6%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04282365uspto-grants-1981_08