Acetic Anhydride → HCID 68147254, compound

HRID 1606273Notes

Reaction equation

HRID 1606273 reaction equation
C(O[C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16]([O:23]C(=O)C)=[CH:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:27][C:28](=[O:30])[CH3:29])[CH:6]=1)(=O)C.C([O:34][C:35](=[O:37])[CH3:36])(=O)C.[C:38]([O-:41])(=[O:40])[CH3:39].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[C:38]([O:41][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[C@@H:15]([O:34][C:35](=[O:37])[CH3:36])[CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:27][C:28](=[O:30])[CH3:29])[CH:6]=1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 68147543HCID 68147543, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 68147254HCID 68147254, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Two grams of rac.-1,3,17-triacetoxy-8α-estra-1,3,5(10),16-tetraene is agitated in 40 ml. of glacial acetic acid and 2 ml. of acetic anhydride with 5.5 g. of lead tetraacetate for 15 hours at room temperature. The mixture is evaporated in a forced circulation evaporator. The residue is taken up in ethyl acetate and washed neutral with saturated sodium chloride solution. By preparative thin-layer chromatography, minor amounts of starting material are separated. After elution with acetone, the mixture is afteracetylated with acetic anhydride and pyridine. After working up the reaction mixture and recrsytallization from methylene chloride/isopropyl ether, 700 mg. of rac.-1,3,16β-triacetoxy-8α-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. customThe mixture is evaporated in a forced circulation evaporator
  2. washwashed neutral with saturated sodium chloride solution
  3. customBy preparative thin-layer chromatography, minor amounts of starting material are separated
  4. washAfter elution with acetone

Sources & evidence

ORD record
ord-22132a803c9d4f2ab14d02cccbdcd98f
Source dataset
uspto-grants-1976_04
Patent number
US03951958

Reaction notes

Loading…