Sodium hydride → Tert-butyl 3-oxo-3-phenylpropoxycarbamate

HRID 2189942Notes

Reaction equation

HRID 2189942 reaction equation
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[H-].[Na+].Cl[CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>C1COCC1>[O:16]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:14][CH2:13][O:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 702953-ChloropropiophenoneHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 86639135Tert-butyl 3-oxo-3-phenylpropoxycarbamateYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of tert-butyl hydroxycarbamate (1.90 g, 14.2 mmol) in THF (30 mL) was added NaH (0.285 g, 11.9 mmol). After stirring at 0° C. for 5 minutes and at room temperature for 10 minutes, the mixture was added to a solution of 3-chloro-1-phenylpropan-1-one (2.00 g, 11.9 mmol) in THF (10 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 (20% ethyl acetate in hexanes) to provide the product (2.20 g, 69%) as a white solid.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was chromatographed (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9e6890961e3b4ec19c2656df3da4cdd1
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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