Benzene → HCID 86733487, compound

HRID 1415036Notes

Reaction equation

HRID 1415036 reaction equation
[C:1]1(C)C=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C1C=CC=CC=1.[OH:18][C@@H:19]1[C@:27]2([CH2:28][CH3:29])[C@H:22]([C@@H:23]3[CH2:37][CH2:36][C:35]4[C@H:30]([CH2:31][CH2:32][C:33](=[O:38])[CH:34]=4)[C@H:24]3[CH2:25][CH2:26]2)[CH2:21][CH2:20]1.[OH-:39].[Na+]>O1C=CCCC1.CO.O>[CH2:28]([C@:27]12[CH2:26][CH2:25][C@@H:24]3[C@@H:30]4[C:35]([CH2:36][CH2:37][C@H:23]3[C@@H:22]1[CH2:21][CH2:20][C@@H:19]2[O:18][CH:5]1[CH2:4][CH2:3][CH2:2][CH2:1][O:39]1)=[CH:34][C:33](=[O:38])[CH2:32][CH2:31]4)[CH3:29]

Participants

8

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Product 1

HCID 86733487HCID 86733487, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 80803,4-dihydro-2H-pyranSolvent

Procedure

Add with swirling a solution of p-toluenesulfonic acid (14 mg) in benzene (0.8 mole) to dl-17β-hydroxy-13-ethylgon-4-en-3-one (450 mg) in 2,3-dihydropyran (3 ml). After 2 hours, neutralize the reaction mixture with methanolic sodium hydroxide. Add water, together with some methanol, scratch the mixture and allow it to stand at 0° for about 70 hours. Filter to obtain the title compound (100 mg), m.p. 148°-152°; infrared absorption peaks at 6.0 μ, 6.2 μ, 9.02 μ, 9.42 μ, 9.68 μ, 9.85 μ, 10.25 μ (no hydroxyl band).

Workup

  1. additionAdd
  2. waitto stand at 0° for about 70 hours
  3. filtrationFilter

Sources & evidence

ORD record
ord-6afe2f05530a4b888f3405316897fe63
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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