Sodium hydride → [4-(2-oxo-2H-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester

HRID 1884612Notes

Reaction equation

HRID 1884612 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:21])[NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([OH:20])=[CH:12][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].Cl[C:23]1[CH:28]=[CH:27][O:26][C:25](=[O:29])[CH:24]=1>C1COCC1>[C:3]([O:7][C:8](=[O:21])[NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([O:20][C:23]2[CH:28]=[CH:27][O:26][C:25](=[O:29])[CH:24]=2)=[CH:12][CH:11]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamateHCID 109314664-Chloro-2H-pyran-2-one

Product 1

HCID 11439599[4-(2-oxo-2H-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (0.070 g of 60% oil dispersion) in 5 mL of anhydrous THF at 0° C. was added (4-hydroxy-naphthalen-1-yl)-carbamic acid tert-butyl ester (0.414 g) (Example 5). The mixture was stirred 20 min, then 4-chloro-2H-pyran-2-one (Helvitica Chemica. Acta, 1990, 73, 883) (0.208 g) was added and the reaction stirred 5 h at 0° C. Removal of the volatiles in vacuo provided a residue which was purified by flash chromatography on silica gel eluting with 33% EtOAc in hexanes. Concentration of the product rich fractions provided [4-(2-oxo-2H-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester.

Workup

  1. stirringthe reaction stirred 5 h at 0° C
  2. customRemoval of the volatiles in vacuo
  3. customprovided a residue which
  4. customwas purified by flash chromatography on silica gel eluting with 33% EtOAc in hexanes

Sources & evidence

ORD record
ord-4e1ebed10b944731bfab21fb61b234a9
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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