(+)-Estrone 3-methyl ether → HCID 10087777, compound

HRID 437019Notes

Reaction equation

HRID 437019 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:22]2[C@H:9]3[CH2:10][CH2:11][C@@:12]4([CH3:21])[C@H:16]([C@@H:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=1)[CH2:15][CH2:14][C@@H:13]4[O:17][C:18](=[O:20])[CH3:19].COC1C=CC2[C@H]3CC[C@@]4(C)[C@H]([C@@H]3CCC=2C=1)CCC4=O>>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:22]2[C:9]3=[CH:10][CH2:11][C@@:12]4([CH3:21])[C@H:16]([C@@H:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=1)[CH2:15][CH2:14][C@@H:13]4[O:17][C:18](=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 92895(+)-Estrone 3-methyl etherHCID 112674485976-55-6

Product 1

HCID 10087777HCID 10087777, compound

Procedure

The procedure described in Example 1 hereinbefore was repeated but an equal amount of 3-methoxy-13β-methyl-17β-acetoxygona-1,3,5(10)-triene was substituted for the 3-methoxy-13β-methylgona-1,3,5(10)-trien-17-one that was used in that example. After distilling off the dichloromethane from the electrolyzed solution at a subatmospheric pressure and crystallizing from the remaining solution, 2.0 grams of 3-methoxy-13β-methyl-17β-acetoxygona-1,3,5(10),9(11)-tetraene having a melting point of 110°-113° C., was obtained. After recrystallization of the compound from a mixture of dichloromethane and methanol it had a melting point of 114°-116° C. and a specific optical rotation of +95° at a temperature of 25° C. for the sodium D line.

Workup

  1. distillationAfter distilling off the dichloromethane from the electrolyzed solution at a subatmospheric pressure
  2. customcrystallizing from the remaining solution, 2.0 grams of 3-methoxy-13β-methyl-17β-acetoxygona-1,3,5(10),9(11)-tetraene having a melting point of 110°-113° C.
  3. customwas obtained
  4. customAfter recrystallization of the compound
  5. additionfrom a mixture of dichloromethane and methanol it
  6. customa specific optical rotation of +95°
  7. customat a temperature of 25° C.

Sources & evidence

ORD record
ord-996b425bc02a4a71a27c629ee4fab660
Source dataset
uspto-grants-1977_06
Patent number
US04029648

Reaction notes

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