Hydrochloric Acid → HCID 10322530, compound

HRID 1394529Notes

Reaction equation

HRID 1394529 reaction equation
[CH3:1][C:2]1([CH3:32])[C:11]2[CH:10]=[C:9]([Se:12][C:13]#[C:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)[CH:8]=[CH:7][C:6]=2[C:5]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[CH:4][CH2:3]1.C(O)C.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH3:1][C:2]1([CH3:32])[C:11]2[CH:10]=[C:9]([Se:12][C:13]#[C:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)[CH:8]=[CH:7][C:6]=2[C:5]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)=[CH:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 11511426HCID 11511426, compound

Product 1

HCID 10322530HCID 10322530, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.46 g (0.95 mmol) of methyl 4-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-2-naphthylselanylethynyl)benzoate is dissolved in 20 ml of tetrahydrofuran, 2 ml of ethanol and 1 ml of water, and 0.46 g (11 mmol) of lithium hydroxide monohydrate is then added. The reaction medium is refluxed for 15 hours, acidified with 2N hydrochloric acid solution and then extracted with ethyl acetate. The solid obtained is washed with a heptane/ethyl ether mixture (90/10) and then purified by chromatography (eluent: dichloromethane). An off-white powder is obtained (0.2 g; yield=45%).

Workup

  1. temperatureThe reaction medium is refluxed for 15 hours
  2. extractionextracted with ethyl acetate
  3. customThe solid obtained
  4. washis washed with a heptane/ethyl ether mixture (90/10)
  5. custompurified by chromatography (eluent: dichloromethane)
  6. customAn off-white powder is obtained (0.2 g; yield=45%)

Sources & evidence

ORD record
ord-f0d9d3d313274f799b7f7449f9e97ccb
Source dataset
uspto-grants-2008_03
Patent number
US07348449B2

Reaction notes

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