Sodium hydride → 4-(2-(Benzyloxy)ethyl)morpholin-3-one

HRID 601531Notes

Reaction equation

HRID 601531 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]1=[O:9].Br[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.O>[CH2:14]([O:13][CH2:12][CH2:11][N:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]1=[O:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 73833Benzene, ((2-bromoethoxy)methyl)-

Product 1

HCID 574214944-(2-(Benzyloxy)ethyl)morpholin-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add NaH (0.47 g, 11.8 mmol) to a solution of morpholin-3-one (Vieles, P.; Seguin, J., Bulletin de la Societe Chimique de France, 1953, 287-9) (1.0 g, 9.9 mmol) in DMF (10 ml) at room temperature. Stir for 30 min, add (2-bromo-ethoxymethyl)-benzene (2.2 g, 10.2 mmol), and stir at room temperature for 18 h. Dilute with water and extract with EtOAc (2×). Combine the organics, dry, and concentrate. Purify by flash chromatography using 0-5% MeOH in CH2Cl2, to give the product as an oil. (1.7 g, 74%). 1H NMR (400 MHz, CDCl3): δ 7.28 (m, 5H), 4.48 (s, 2H), 4.13 (s, 2H), 3.80 (t, 2H, J=5.1 Hz), 3.65 (m, 2H), 3.59 (dd, 2H, J=7.5, 2.6 Hz), 3.48 (t, 2H, J=5.1 Hz).

Workup

  1. stirringstir at room temperature for 18 h
  2. extractionextract with EtOAc (2×)
  3. customCombine the organics, dry
  4. concentrationconcentrate
  5. customPurify by flash chromatography

Sources & evidence

ORD record
ord-80413074acbd4020b15fc12337d1cec2
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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