Tetrahydrofuran → HCID 54408398, compound

HRID 1657358Notes

Reaction equation

HRID 1657358 reaction equation
[C:1]([O:4][C@H:5]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:11]3[CH2:12][CH2:13][C:14]2=[C:15]([C:19]#[N:20])[C:16]([OH:18])=[O:17])[CH2:6]1)(=[O:3])[CH3:2].O1CCCC1.[OH-].[Na+].[H][H]>[Pd].C(O)C>[C:1]([O:4][C@H:5]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([C:19]#[N:20])[C:16]([OH:18])=[O:17])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 54062734HCID 54062734, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54408398HCID 54408398, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

37 g. of the ethyl ester of 3β-acetoxy-20-cyano-5,17(20)-pregnadiene-21-oic acid is mixed in 450 ml. of tetrahydrofuran and 150 ml. of ethanol with 2.5 g. of 10% palladium-charcoal catalyst and 2 ml. of N/10 sodium hydroxide solution and hydrogenated under normal pressure with hydrogen at room temperature. The reaction mixture is worked up as set forth in Example 1(b), thus obtaining the ethyl ester of 3β-acetoxy-20-cyano-5-pregnene-21-oic acid (34 g.), m.p. 170° C.

Sources & evidence

ORD record
ord-4b1dbe58e8e5437a90f44a0cee230799
Source dataset
uspto-grants-1976_06
Patent number
US03960842

Reaction notes

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