Benzyl Alcohol → HCID 12800135, compound

HRID 1680133Notes

Reaction equation

HRID 1680133 reaction equation
[CH3:1][C@:2]12[CH2:21][CH2:20][C@H:19]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@:17]3([CH3:18])[CH2:16][CH2:15][C:13](=[O:14])[CH:12]=4)[C@@H:7]1[CH2:6][CH2:5][C:3]2=[O:4].C(OCC)(OCC)OCC.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35](S(O)(=O)=O)=[CH:34][CH:33]=1.C(O)C1C=CC=CC=1>C1C=CC=CC=1>[CH2:42]([O:14][C:13]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C:11](=[CH:10][CH2:9][C@@H:8]3[C@@H:19]2[CH2:20][CH2:21][C@@:2]2([CH3:1])[C@H:7]3[CH2:6][CH2:5][C:3]2=[O:4])[CH:12]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 6128AndrostenedioneHCID 31214Ethyl orthoformate

Product 1

HCID 12800135HCID 12800135, compoundYield 12,348.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Androstenedione (5 g) was dissolved in dry benzene (100 ml). Triethyl orthoformate (3.25 ml) was added, followed by p-toluenesulphonic acid (20 mg) and the solution heated at 50° for 45 minutes. Benzyl alcohol (7.5 ml) and benzene (150 ml) were then added and the solution distilled until 150 ml of distillate had been collected. A few drops of pyridine were added and the solution evaporated under reduced pressure to give a yellow solid. This solid was recrystallised from ethanol to give 3-benzyloxy-androsta-3,5-dien-17-one (5.4 g) as white needles, M.p. 172°-178°.

Workup

  1. temperaturethe solution heated at 50° for 45 minutes
  2. distillationthe solution distilled until 150 ml of distillate
  3. customhad been collected
  4. additionA few drops of pyridine were added
  5. customthe solution evaporated under reduced pressure
  6. customto give a yellow solid
  7. customThis solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-e241b9e6e40e4790bab700b9638bc1f1
Source dataset
uspto-grants-1981_06
Patent number
US04272445

Reaction notes

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