Isovaleryl chloride → HCID 68144173, compound

HRID 1415011Notes

Reaction equation

HRID 1415011 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:27])[CH2:23][CH:24]([CH3:26])[CH3:25]>N1C=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:27])[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

4

Reactant 2

HCID 66054Isovaleryl chlorideHCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Product 1

HCID 68144173HCID 68144173, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Keep 13β-ethyl-17β-hydroxy-gon-4-en-3-one (6 g.) with isovaleroyl chloride (7.2 g.) in pyridine at room temperature for 20 hours. Add aqueous sodium bicarbonate and extract the product with ether. Wash, dry and evaporate the extracts and purify the residue by chromatography upon neutral alumina. Distill at 200°-230°/.01 mm. and crystallize from hexane to obtain the title compound, m.p. 82°- 89°; ultraviolet absorption peak at 240 mμ (ε15,650); infrared absorption peaks at 5.76, 5.99, 6.18 μ.

Workup

  1. customat room temperature
  2. customfor 20 hours
  3. extractionAdd aqueous sodium bicarbonate and extract the product with ether
  4. washWash
  5. customdry
  6. customevaporate the extracts
  7. custompurify the residue by chromatography upon neutral alumina
  8. distillationDistill at 200°-230°/.01 mm
  9. customand crystallize from hexane

Sources & evidence

ORD record
ord-b3a47a2b34834d6e84adf58ef11a67f9
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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