HCID 20726820, compound → HCID 11200823, compound

HRID 460466Notes

Reaction equation

HRID 460466 reaction equation
[O:1]([C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:10]12[CH3:11])[C:23]1[CH:22]=[CH:21][C:20]([O:27][CH3:28])=[CH:19][C:18]=1[CH:17]([OH:29])[CH2:16]3)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]>ClCCl.[O-2].[O-2].[Mn+4]>[O:1]([C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:24]([CH2:25][CH2:26][C@:10]12[CH3:11])[C:23]1[CH:22]=[CH:21][C:20]([O:27][CH3:28])=[CH:19][C:18]=1[C:17](=[O:29])[CH2:16]3)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 20726820HCID 20726820, compound

Product 1

HCID 11200823HCID 11200823, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

17β-(t-Butyldimethylsiloxy)-3-methoxyestra-1,3,5(10)-trien-6-ol (14.4 g, 34.5 mmol) was dissolved in dichloromethane (250 ml). Manganese dioxide (29 g) and molecular sieves 4A powder (7.2 g) were added to the resulting solution followed by stirring for 1 hour at room temperature. The reaction mixture was filtered through cellite and the filtrate was concentrated under reduced pressure. The residue was recrystallized from hexane to give 17β-(t-butyldimethylsiloxy)-3-methoxyestra-1,3,5(10)-trien-6-one (11.36 g, Yield 79%).

Workup

  1. filtrationThe reaction mixture was filtered through cellite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-d2472c61d0d542d6b06ff66510000125
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

Loading…