Tetrahydrofuran → 3-Hydroxy-17-[(4-methylpentyl)oxy]androst-5-en-7-one

HRID 1703775Notes

Reaction equation

HRID 1703775 reaction equation
[CH3:1][CH:2]([CH3:27])[CH2:3][CH2:4][CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:9])[C@:21]1([CH3:22])[C:16]([CH2:17][CH2:18][CH2:19][CH2:20]1)=[CH:15][C:14]3=[O:26].[O:28]1CCCC1>O>[OH:28][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C:16](=[CH:15][C:14](=[O:26])[C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:8]2([CH3:9])[C@H:10]3[CH2:11][CH2:12][C@@H:7]2[O:6][CH2:5][CH2:4][CH2:3][CH:2]([CH3:27])[CH3:1])[CH2:17]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 86736150HCID 86736150, compound

Product 1

HCID 1942463-Hydroxy-17-[(4-methylpentyl)oxy]androst-5-en-7-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3 parts of 3β-{(1,1-dimethylethyl)dimethylsilyl] oxy}-17β-[(4-methylpentyl)oxy]androst-5-en-7-one, 45 parts of tetrahydrofuran, 15 parts of acid, and 10 parts of water is heated at approximately 60° for 48 hours, whereupon 300 parts of water is added and the resultant mixture is extracted with 1,1'-oxybisethane. The extract is washed with aqueous 5% potassium bicarbonate, dried over magnesium sulfate, and strippd of solvent by vacuum distillation. The residue is chromatographed on silica gel, using mixtures of benzene and ethyl actate (initially comprising 10% ethyl acetate and progressively increasing the proportions thereof to 25%) as developing solvent. Eluates are selected via thin layer chromatography which, upon evaporation of solvent and recrystallization of the residues from a mixture of 1,1'-oxybisethane and hexane, afford 3β-hydroxy-17β-[(4-methylpentyl)oxy]androst-5en-7-one melting at approximately 133.5°-134.5°. The product has the formula ##STR8##

Workup

  1. additionis added
  2. extractionthe resultant mixture is extracted with 1,1'-oxybisethane
  3. washThe extract is washed with aqueous 5% potassium bicarbonate
  4. dry with materialdried over magnesium sulfate, and strippd of solvent by vacuum distillation
  5. customThe residue is chromatographed on silica gel
  6. temperatureprogressively increasing the proportions
  7. customEluates are selected via thin layer chromatography which, upon evaporation of solvent and recrystallization of the residues from a mixture of 1,1'-oxybisethane and hexane

Sources & evidence

ORD record
ord-b53f89b05f394666ba541265840c2429
Source dataset
uspto-grants-1978_11
Patent number
US04125544

Reaction notes

Loading…