Hydrochloric Acid → HCID 57563433, compound

HRID 1726318Notes

Reaction equation

HRID 1726318 reaction equation
[Li].[H-].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][C:14]1[CH:23]=[C:22]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:15]=1[C:16](OC)=[O:17].Cl>C(OCC)C.O1CCCC1>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][C:14]1[CH:23]=[C:22]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:15]=1[CH2:16][OH:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 166653HydrideHCID 3028194LithiumHCID 23016889HCID 23016889, compound

Product 1

HCID 57563433HCID 57563433, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of zinc (710 mg) in tetrahydrofuran (2 ml) was added dibromoethane (1 drop) under an atmosphere of argon. The mixture was heated and then added trimethylsilyl chloride (1 drop). The reaction mixture was cooled to 0° C. and added dropwise a solution of 2-bromomethylnaphthalene (1.20 g) in tetrahydrofuran (3 ml). The mixture was stirred at room temperature for 1.5 hour to give the zinc reagent. To a solution of [bis(benzylidene)acetone]palladium (156 mg) and diphenylphosphinoferrocene (151 mg) in tetrahydrofuran (2 ml) was added the compound prepared in Reference Example 17 (1.00 g) in tetrahydrofuran (3 ml) under an atmosphere of argon. To the mixture was added the above-mentioned zinc reagent. The mixture was stirred at room temperature for 30 minutes. To the mixture was added a saturated aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel to give methyl 2-(2-naphthylmethyl)-4-phenoxymethylbenzoate. To a suspension of lithium alminium hydride (206 mg) in (2 ml) was added dropwise a solution of the above-mentioned methyl 2-(2-naphthylmethyl)-4-phenoxymethylbenzoate in diethyl ether (3 ml)-tetrahydrofuran (3 ml) under an atmosphere of argon. The mixture was stirred for 30 minutes. To the mixture was added 1N hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (974 mg) having the following physical data.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5771d3220f5f4d72856b9c9012e609e2
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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