Sodium hydride → HCID 86639137, compound

HRID 2189944Notes

Reaction equation

HRID 2189944 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].[H-].[Na+].Cl[CH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>C1COCC1>[CH3:1][O:2][N:3]([CH2:14][CH2:15][C:16](=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 702953-ChloropropiophenoneHCID 12240290tert-butyl N-methoxycarbamate

Product 1

HCID 86639137HCID 86639137, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of tert-butyl methoxycarbamate (2.35 g, 16.0 mmol) in THF (50 mL) was slowly added NaH (0.640 g, 16.0 mmol). After stirring at 0° C. for 5 minutes and then at room temperature for 30 minutes, the mixture was added dropwise to a solution of 3-chloro-1-phenylpropan-1-one (2.84 g, 16.8 mmol) in THF (25 mL). After stirring at room temperature for 30 minutes, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was chromatographed (10% ethyl acetate in hexanes) to provide the product (1.80 g, 40% yield) as a clear oil.

Workup

  1. waitat room temperature for 30 minutes
  2. stirringAfter stirring at room temperature for 30 minutes
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-bb23012484cb48848537252d700e7aec
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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