Hydrochloric Acid → HCID 68144268, compound

HRID 1415015Notes

Reaction equation

HRID 1415015 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>N1C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Product 1

HCID 68144268HCID 68144268, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1049PyridineSolvent

Procedure

Treat 13β-ethyl-17β-hydroxy-gon-4-en-3-one (2 g.) in pyridine (20 cc.) with benzoyl chloride (3 cc.) in benzene (10 cc.) at -10°. Keep the mixture at that temperature for 18 hours and then pour into 2N hydrochloric acid (200 cc.). Extract the product with ether and wash, dry and evaporate the extracts. Triturate the residue with a mixture of ether and hexane. Filter the crystalline material obtained and dissolve in benzene and purify by chromatography on neutral alumina. Recrystallize from a mixture of ethyl acetate and hexane to give the title compound, m.p. 141°-9°; ultraviolet light absorption peak at 237 mμ (ε27,300).

Workup

  1. customfor 18 hours
  2. extractionExtract the product with ether
  3. washwash
  4. customdry
  5. customevaporate the extracts
  6. customTriturate the residue
  7. additionwith a mixture of ether and hexane
  8. filtrationFilter the crystalline material
  9. customobtained
  10. custompurify by chromatography on neutral alumina
  11. customRecrystallize from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-8c8a840a13f24a74a484e830f88cc24f
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

Loading…