Hydrochloric Acid → HCID 21697102, compound

HRID 379039Notes

Reaction equation

HRID 379039 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[CH:5]=1.[Li+].[BH4-].O.Cl>C1COCC1>[I:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][C:6]=1[O:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 539211574-Iodo-3-(naphthalen-2-yloxy)-benzoic acid methyl ester

Product 1

HCID 21697102HCID 21697102, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Iodo-3-(naphthalen-2-yloxy)-benzoic acid methyl ester (0.10 g, 0.25 mmol) dissolved in THF (2 mL) was treated with LiBH4 (2 M solution in THF) (0.247 mL, 0.495 mmol) and heated at reflux for 1.5 hr. The reaction mixture was cooled, added to H2O (50 mL)- concd HCl (4.3 mL), and extracted with EtOAc (3×30 mL). The organics were combined, washed with H2O, aq saturated NaHCO3 solution, brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound which was used without purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with EtOAc (3×30 mL)
  5. washwashed with H2O, aq saturated NaHCO3 solution, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-070f5b911b604575881b4138dfcb6ac2
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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