1-Naphthol → HCID 57141760, compound

HRID 1066040Notes

Reaction equation

HRID 1066040 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@H:4](Br)[CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[C:19]1([OH:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([O:29][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 54364258HCID 54364258, compound

Product 1

HCID 57141760HCID 57141760, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R)-2-bromo-4-carbobenzyloxy-butyric acid methyl ester (1.00 g, 3.17 mmol) and 1-naphthol (0.500 g, 3.47 mmol) in dimethylformamide (4.0 mL) at room temperature under nitrogen was added powdered anhydrous K2CO3 (0.560 g, 4.7 mmol). After stirring at room temperature for 3.5 hrs, the mixture was partitioned between EtOAc-water. The organic phase was washed with water, 5% KHSO4 and saturated NaCl solutions, dried over anhydrous Na2SO4 and evaporated to a yellow oil. The crude product was purified by flash chromatography on silica gel eluting with Et2O-hexane(1:4) to give the title compound (1.105 g, 92%) as a pale yellow oil. TLC(Et2O-hexane; 3:7; 2 developments) Rf=0.33 (bromide Rf=0.52; 1-naphthol Rf=0.41).

Workup

  1. customthe mixture was partitioned between EtOAc-water
  2. washThe organic phase was washed with water, 5% KHSO4 and saturated NaCl solutions
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated to a yellow oil
  5. customThe crude product was purified by flash chromatography on silica gel eluting with Et2O-hexane(1:4)

Sources & evidence

ORD record
ord-ca066303c0a24f7fa3fd00aeb3785d43
Source dataset
uspto-grants-2001_06
Patent number
US06242422B1

Reaction notes

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