HCID 15767572, compound → HCID 70631916, compound

HRID 437020Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:24]=[CH:23][C:22]2[C@H:12]3[CH2:13][CH2:14][C@@:15]4([CH3:21])[C@H:19]([C@@H:11]3[CH2:10][CH2:9][C:8]=2[CH:7]=1)[CH2:18][CH2:17][C:16]4=[O:20])[CH:2]([CH3:4])[CH3:3].C(OC1C=CC2[C@H]3CC[C@@]4(C)[C@H]([C@@H]3CCC=2C=1)CCC4=O)CC>>[CH2:1]([O:5][C:6]1[CH:24]=[CH:23][C:22]2[C:12]3=[CH:13][CH2:14][C@@:15]4([CH3:21])[C@H:19]([C@@H:11]3[CH2:10][CH2:9][C:8]=2[CH:7]=1)[CH2:18][CH2:17][C:16]4=[O:20])[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 15767572HCID 15767572, compound

HCID 70632249HCID 70632249, compound

Product 1

HCID 70631916HCID 70631916, compoundYield 80.5%

Procedure

The procedure described in Example 10 hereinbefore was repeated except that 1 gram of 3-isobutoxy-13β-methylgona-1,3,5(10)-trien-17-one was substituted for the 3-n-propoxy-13β-methylgona-1,3,5(10)-trien-17-one that was used in that example. In this manner, 0.8 gram of 3-isobutoxy-13β-methylgona-1,3,5(10),9(11)-tetraen-17-one was obtained after distillation of the dichloromethane from the electrolyzed solution and precipitation by adding a small amount of water to the remaining solution. This compound, after recrystallization from a mixture of dichloromethane and methanol, had a melting point of 107°-108° C. and a specific optical rotation of +257.5° at a temperature of 25° C. for the sodium D line.

Sources & evidence

ORD record: ord-3f198d6c5fe942389228bbf2b1d8ff0a
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04029648

Reaction notes

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