tert-Butanol → HCID 14257195, compound

HRID 1650118Notes

Reaction equation

HRID 1650118 reaction equation
[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:18]([C:19]=2[CH2:20][CH:21]=1)[CH2:17][CH2:16][C@@:13]1([CH2:14][CH3:15])[C@H:9]3[CH:10]=[CH:11][C@@H:12]1[OH:22].C(O)(C)(C)C>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:18]([C:19]=2[CH2:20][CH:21]=1)[CH2:17][CH2:16][C@@:13]1([CH2:14][CH3:15])[C@H:9]3[CH:10]=[CH:11][C:12]1=[O:22]

Participants

5

Reactant 2

HCID 6386tert-ButanolHCID 14257193HCID 14257193, compound

Product 1

HCID 14257195HCID 14257195, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent2×

Procedure

4.7 g of 3-methoxy-18-methyl-2,5(10),15-estratrien-17β-ol is refluxed for 18 hours in 250 ml of chloroform and 35 ml of t-butanol with 10 g of manganese dioxide. The product is suctioned off over Celite, rewashed with chloroform and concentrated under reduced pressure. After chromatographic purification on silica gel with hexane/ethyl acetate, 4.1 g of pure 3-methoxy-18-methyl-2,5(10),15-estratrien-17-one with a melting point of 89°-91° C. is obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customAfter chromatographic purification on silica gel with hexane/ethyl acetate, 4.1 g of pure 3-methoxy-18-methyl-2,5(10),15-estratrien-17-one with a melting point of 89°-91° C.
  3. customis obtained

Sources & evidence

ORD record
ord-0ec2ca00c92c42ed9a28f8f68c76a450
Source dataset
uspto-grants-1990_05
Patent number
US04923640

Reaction notes

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