Tetrahydrofuran → HCID 54006954, compound
Reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:24]2[CH:23]=[C:22]([OH:25])[CH:21]=[CH:20][C:19]=2[C@@H:18]2[C@H:9]([C@H:10]3[C@@:14]([CH2:16][CH2:17]2)([CH3:15])[C@@H:13]([OH:26])[CH2:12][CH2:11]3)[CH:8]=1)=[O:5])[CH3:2].O1CCCC1.[H][H].C(OC(C[C@H]1C2C=C(O)C=CC=2[C@@H]2[C@H]([C@H]3[C@@](CC2)(C)[C@@H](O)CC3)C1)=O)C>[Pd].C([O-])([O-])=O.[Ca+2].CO>[CH2:1]([O:3][C:4]([CH:6]=[C:7]1[C:24]2[CH:23]=[C:22]([OH:25])[CH:21]=[CH:20][C:19]=2[C@@H:18]2[C@H:9]([C@H:10]3[C@@:14]([CH2:16][CH2:17]2)([CH3:15])[C@@H:13]([OH:26])[CH2:12][CH2:11]3)[CH2:8]1)=[O:5])[CH3:2]Participants
Procedure
20 g. of 6-ethoxycarbonylmethyl-1,3,5(10),6-estratetraene-3,17β-diol is hydrogenated in 280 ml. of tetrahydrofuran and 280 ml. of methanol in the presence of 2 g. of Pd/CaCO3 (10%) until 1 millimole of hydrogen has been absorbed per millimole of substance. The thus-obtained product is 6β-ethoxycarbonylmethyl-1,3,5(10)-estratriene-3,17β-diol as a foamy mass. The same compound is also produced by the analogous hydrogenation of 6-ethoxycarbonylmethylene-1,3,5(10)-estratriene-3,17β-diol. The preparation of 6β-ethoxycarbonylmethyl-1,3,5(10)-estratriene-3,17β-diol can be simplified by hydrolyzing the crude product of the Reformatskii reaction, freeing the thus-obtained hydrolyzate from by-products by fractional filtration over silica gel, and hydrogenating the evolved mixture of 6-ethoxycarbonylmethyl-1,3,-5(10),6-estratetraene-3,17β-diol and 6-ethoxycarbonylmethylene-1,3,5(10)-estratriene-3,17β-diol as indicated above.
Sources & evidence
- ORD record
- ord-04eaf81929c3482c84d6cf29c0238eb3
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03935245
Reaction notes
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