Hydrochloric Acid → HCID 10074177, compound

HRID 735381Notes

Reaction equation

HRID 735381 reaction equation
[CH3:1][C:2]1([CH3:33])[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])=[C:17]([OH:25])[CH:16]=3)[CH:8]=[CH:7][C:6]=2[C:5]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[CH:4][CH2:3]1.[OH-].[Na+].Cl>O1CCCC1>[CH3:1][C:2]1([CH3:33])[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])=[C:17]([OH:25])[CH:16]=3)[CH:8]=[CH:7][C:6]=2[C:5]([C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86601146HCID 86601146, compound

Product 1

HCID 10074177HCID 10074177, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

1.1 g (2 mmol) of methyl 4-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-2-naphthylselanylethynyl)-2-hydroxybenzoate (described in Example 5b) are dissolved in 10 ml of tetrahydrofuran, and 0.96 g (24 mmol) of sodium hydroxide is then added. The reaction medium is heated at 100° C. for 14 hours, acidified with 2N hydrochloric acid solution and then extracted with ethyl ether. The residue obtained is purified by chromatography (eluent: 7/3 heptane/ethyl acetate). After recrystallization from a heptane/ethyl ether mixture, a white solid is obtained (0.65 g; yield=61%; m.p.=201° C.).

Workup

  1. extractionextracted with ethyl ether
  2. customThe residue obtained
  3. customis purified by chromatography (eluent: 7/3 heptane/ethyl acetate)
  4. customAfter recrystallization from a heptane/ethyl ether mixture
  5. customa white solid is obtained (0.65 g; yield=61%; m.p.=201° C.)

Sources & evidence

ORD record
ord-e16a6bb0ef974505947d0d4856b45de3
Source dataset
uspto-grants-2009_09
Patent number
US07592478B2

Reaction notes

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