Water → HCID 68131075, compound

HRID 1973499Notes

Reaction equation

HRID 1973499 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][CH:15]3[OH:20])[C@@H:11]1[CH2:10][CH2:9][C:8]1[CH2:7][C:6]([OH:21])=[CH:5][CH2:4][C:3]2=1.[CH3:22]C(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].O.[OH-].[Na+]>C1C=CC=CC=1.CC(=O)CC>[CH3:22][O:21][C:6]1[CH2:7][C:8]2[CH2:9][CH2:10][C@@H:11]3[C@@:2]([CH3:1])([C:3]=2[CH2:4][CH:5]=1)[CH2:19][CH2:18][C@@:16]1([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]1=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 11143Aluminum isopropoxideHCID 14798Sodium HydroxideHCID 68130134HCID 68130134, compound

Product 1

HCID 68131075HCID 68131075, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5.0 g of 9alpha-methylestra-2,5(10)-dien-3,17-diol 3 methyl ether and 4.5 g of aluminum isopropoxide in 45 ml of benzene and 45 ml of 2-butanone is stirred and refluxed for 22 hrs., using a water separator. After cooling, the reaction mixture is added to 100 ml. of 2N sodium hydroxide solution and a further 50 ml. of benzene are added. The organic layer is separated, washed with water and saturated sodium chloride and dried over anhydrous sodium sulphate. Removal of the solvent gives a residue which is crystallized from ether/hexane, 1/1 yielding 3-methoxy-9alpha-methyl-estra-2,5(10)-dien-17-one, m.p. 155°-158°, which may be used in Step H, below. Recrystallization from ether yields a product of m.p. 175°-177°.

Workup

  1. temperaturerefluxed for 22 hrs
  2. temperatureAfter cooling
  3. additionthe reaction mixture is added to 100 ml
  4. customThe organic layer is separated
  5. washwashed with water and saturated sodium chloride
  6. dry with materialdried over anhydrous sodium sulphate
  7. customRemoval of the solvent
  8. customgives a residue which
  9. customis crystallized from ether/hexane, 1/1 yielding 3-methoxy-9alpha-methyl-estra-2,5(10)-dien-17-one, m.p. 155°-158°, which
  10. customRecrystallization from ether
  11. customyields a product of m.p. 175°-177°

Sources & evidence

ORD record
ord-c82b7f373a934bebbb3cf3bd677314c8
Source dataset
uspto-grants-1976_12
Patent number
US03997574

Reaction notes

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