Hydrochloric Acid → HCID 9984642, compound

HRID 2053484Notes

Reaction equation

HRID 2053484 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[CH2:5][O:6][C:7]1[C:16]2[C:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][C:12]([CH3:20])([CH3:19])[C:11]=2[CH:10]=[C:9]([Se:21][C:22]#[C:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=2)[CH:8]=1.O.[OH-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[CH2:5][O:6][C:7]1[C:16]2[C:15]([CH3:17])([CH3:18])[CH2:14][CH2:13][C:12]([CH3:19])([CH3:20])[C:11]=2[CH:10]=[C:9]([Se:21][C:22]#[C:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86599527HCID 86599527, compound

Product 1

HCID 9984642HCID 9984642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

650 mg (1.2 mmol) of methyl 4-[4-(3-fluorobenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylselanylethynyl]benzoate are dissolved in 20 mL of THF. 10 mL of water are added, followed by addition of 240 mg (6 mmol) of sodium hydroxide. The medium is stirred for 4 hours at 80° C. and then acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The residue obtained is purified by chromatography (eluent: 1/1 heptane/ethyl acetate) and then recrystallized in a heptane/ethyl acetate mixture. A pure yellow crystalline solid is obtained (m=577 mg; yield=90%; m.p.=206° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe residue obtained
  3. customis purified by chromatography (eluent: 1/1 heptane/ethyl acetate)
  4. customrecrystallized in a heptane/ethyl acetate mixture
  5. customA pure yellow crystalline solid is obtained (m=577 mg

Sources & evidence

ORD record
ord-65cb05a2e68f4be99ed7e40bca95e5ac
Source dataset
uspto-grants-2008_02
Patent number
US07326803B2

Reaction notes

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