Water → HCID 178445663, compound

HRID 1709151Notes

Reaction equation

HRID 1709151 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:27][C@@:28]12[C@@H:36]([OH:37])[CH2:35][CH2:34][C@H:33]1[C@@H:32]1[CH2:38][CH2:39][C:40]3[C@@:46]([CH3:47])([C@H:31]1[CH2:30][CH2:29]2)[CH2:45][CH2:44][C:42](=[O:43])[CH:41]=3.O>ClCCl.C(O)C>[CH3:27][C@@:28]12[C@@H:36]([OH:37])[CH2:35][CH2:34][C@H:33]1[C@@H:32]1[CH2:38][CH2:39][C:40]3[C@@:46]([CH3:47])([C@H:31]1[CH2:30][CH2:29]2)[CH2:45][CH2:44][C:42](=[O:43])[CH:41]=3.[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([O-:13])=[O:12])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6013TestosteroneHCID 9845Trifluoroacetic anhydrideHCID 178445662HCID 178445662, compound

Product 1

HCID 178445663HCID 178445663, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Trans-4-n-butylcyclohexanecarboxylic acid (11, 50.0 g, 0.27 mol) was added to a solution of trifluoroacetic anhydride (57.0 g, 0.27 mol) in dry dichloromethane (600 ml) and the resulting solution was stirred for 30 min. at 20° C. Testosterone (7, 78.3 g, 0.27 mol) was then added and the mixture was stirred for a further 2 hr at 20° C. After this period, water (500 ml) was added and the two layers were briskly stirred together for 15 min. The dichloromethane layer was separated and washed successively with saturated NaHCO3 (2×250 ml) and then H2O (250 ml). Evaporation of the solvent gave the crude testosterone ester (139.6 g), as an oil which solidified slowly on standing. The solid was dissolved in anhydrous ethanol (140 ml) by warming and the solution was then cooled to 5° C. and held at this temperature for 2 hr. The precipitated solid was filtered and recrystallised twice more from ethanol (70 ml and 80 ml) to give testosterone trans-4-n-butylcyclohexanecarboxylate (65 g, 99.1%) as a white crystalline solid, m.p. 132-134° C. It was identical with the sample prepared by means of Method A.

Workup

  1. stirringthe mixture was stirred for a further 2 hr at 20° C
  2. waitAfter this period
  3. stirringthe two layers were briskly stirred together for 15 min
  4. customThe dichloromethane layer was separated
  5. washwashed successively with saturated NaHCO3 (2×250 ml)
  6. customEvaporation of the solvent
  7. customgave the crude testosterone ester (139.6 g)
  8. temperatureby warming
  9. temperaturethe solution was then cooled to 5° C.
  10. waitheld at this temperature for 2 hr
  11. filtrationThe precipitated solid was filtered
  12. customrecrystallised twice more from ethanol (70 ml and 80 ml)

Sources & evidence

ORD record
ord-2835efce1b854b62b70d9e81cb2298d3
Source dataset
uspto-grants-1990_08
Patent number
US04948790

Reaction notes

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