Hydrochloric Acid → HCID 10787760, compound

HRID 2415233Notes

Reaction equation

HRID 2415233 reaction equation
[OH-].[Li+].[CH3:3][C:4]1([CH3:29])[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]2[CH:9]=[C:8]([Se:16][C:17]#[C:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[CH:7]=[CH:6][C:5]1=2.C(OCC)C.O.Cl>C1COCC1.O.CO>[CH3:3][C:4]1([CH3:29])[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]2[CH:9]=[C:8]([Se:16][C:17]#[C:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=3)[CH:7]=[CH:6][C:5]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21584184Diethylether waterHCID 22641073HCID 22641073, compound

Product 1

HCID 10787760HCID 10787760, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Lithium hydroxide (440 mg) is added to a solution of methyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylselanylethynyl)benzoate (740 mg, 1.74 mmol), obtained in Example 4, in 15 ml of THF and 2 ml of a water/methanol mixture (1/1). The reaction medium is refluxed for 8 h. It is then poured into an ethyl ether/water mixture, acidified to pH 1 with concentrated hydrochloric acid solution and extracted with ethyl ether. After separation of the phases by settling, the organic phase is washed twice with water, dried over anhydrous magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The residue is recrystallized from heptane. After filtration, 615 mg (86%) of a white powder are obtained. m.p.=182° C.

Workup

  1. temperatureThe reaction medium is refluxed for 8 h
  2. extractionextracted with ethyl ether
  3. customAfter separation of the phases
  4. washthe organic phase is washed twice with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  7. customThe residue is recrystallized from heptane
  8. filtrationAfter filtration, 615 mg (86%) of a white powder
  9. customare obtained

Sources & evidence

ORD record
ord-26964bc7162e426cba5df86a24de36f8
Source dataset
uspto-grants-2004_11
Patent number
US06818666B2

Reaction notes

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