Ethyl Acetate → [8-(2-Methoxyethoxy)naphthalen-2-yl]methanol

HRID 252417Notes

Reaction equation

HRID 252417 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[CH:24]=[C:23]([C:26](OC)=[O:27])[CH:22]=[CH:21]2.C(OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl>[CH3:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[CH:24]=[C:23]([CH2:26][OH:27])[CH:22]=[CH:21]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 66888784Methyl 8-(2-methoxyethoxy)naphthalene-2-carboxylate2×

Product 1

HCID 66889067[8-(2-Methoxyethoxy)naphthalen-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.64 ml of diisobutylaluminium hydride (1.5M in toluene) are added dropwise at 0° C. to a solution of 0.26 g of methyl 8-(2-methoxyethoxy)naphthalene-2-carboxylate (residue 35) in 20 ml of dichloromethane. After 3 hours, the reaction solution is admixed with 2 ml of ethyl acetate, stirred for 1 hour, then admixed with 3 ml of I M sodium potassium tartrate solution and subsequently stirred further for 1 hour. The reaction mixture is concentrated by evaporation—the residue is admixed with water and extracted with ethyl acetate (3×). The combined organic phases are washed successively with 1M HCl and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation—the residue
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic phases are washed successively with 1M HCl and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2956f7e183da4859aa3114e5fcda03c0
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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