Acetic Acid → HCID 70626928, compound

HRID 1703776Notes

Reaction equation

HRID 1703776 reaction equation
CC([Si](C)(C)[O:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:9](=[CH:10][C:11](=[O:34])[C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[O:26][CH2:27][CH2:28][CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:8]1)(C)C.O1CCCC1.C(O)(=O)C.[Cl-].[Na+]>O>[OH:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:9](=[CH:10][C:11](=[O:34])[C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[O:26][CH2:27][CH2:28][CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:8]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 22806157HCID 22806157, compound

Product 1

HCID 70626928HCID 70626928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1 part of 3β-{[(1,1-dimethylethyl)dimethylsilyl] oxy}-17β-[(4,4-dimethylpentyl)oxy]androst-5-en-7-one, 22 parts of tetrahydrofuran, 10 parts of acetic acid, and 5 parts of water is heated at approximately 60° under reflux for 48 hours, then poured into 200 parts of water. Approximately 15 parts of sodium chloride is stirred into the resultant mixture. The solid which precipitates is isolated by filtration, washed on the filter with water, dried in air, and finally taken up in 1,1'-oxybisethane. Solvent is thereupon removed by vacuum distillation; and the residue is chromatographed on silicic acid, using benzene and mixtures thereof with increasing amounts of ethyl acetate as developing solvent. Eluates are selected via thin layer chromatography which, upon evaporation of solvent and recrystallization of the residues from a mixture of 2-propanone and hexane, afford 3β-hydroxy-17β-[(4,4-dimethylpentyl)oxy]androst-5-en-7-one melting at 203°-205°. The product has the formula ##STR10##

Workup

  1. temperatureis heated at approximately 60°
  2. temperatureunder reflux for 48 hours
  3. customThe solid which precipitates
  4. customis isolated by filtration
  5. washwashed on the
  6. filtrationfilter with water
  7. customdried in air
  8. customSolvent is thereupon removed by vacuum distillation
  9. customand the residue is chromatographed on silicic acid
  10. customEluates are selected via thin layer chromatography which, upon evaporation of solvent and recrystallization of the residues from a mixture of 2-propanone and hexane

Sources & evidence

ORD record
ord-fe761de04485475fa1f8d84c3044c91d
Source dataset
uspto-grants-1978_11
Patent number
US04125544

Reaction notes

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