N-Formylmorpholine → HCID 18785834, compound

HRID 1107722Notes

Reaction equation

HRID 1107722 reaction equation
C([Li])CCC.[N:6]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1)=[N+:7]=[N-:8].[CH:18](N1CCOCC1)=[O:19]>C1COCC1.C(OCC)C>[N:6]([CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[CH:18]=[O:19])=[N+:7]=[N-:8]

Participants

6

Reactant 3

HCID 20417N-FormylmorpholineHCID 21925012HCID 21925012, compoundHCID 178418339Butyllithium

Product 1

HCID 18785834HCID 18785834, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.50M in hexane, 10.8 mmol, 7.23 ml) was added dropwise at -78° C. to a solution of 1-azido-2-(3-bromophenyl)ethane [Example H(c )] (2.45 g, 10.8 mmol) in THF (80 ml). The bright yellow solution was stirred for 20 min., N-formylmorpholine (2.4 ml) in THF (10 ml) was added dropwise, the solution stirred for a further 30 min. and then warmed room temperature over 1 h. The solution was diluted with diethyl ether, washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over sodium sulphate and evaporated. The residue was purified by flash chromatography, eluting with 10% diethyl ether/hexane, to furnish the product as a pale yellow oil (750 mg). [M-N2 ]+ 146; 360 MHz 1H n.m.r (CDCl3) 10.02 (1H, s), 7.79-7.76 (2H, m), 7.52-7.50 (2H, m), 3.57 (2H, t, J 7.0 Hz), 2.98 (2H, t, J 7.0 Hz).

Workup

  1. stirringthe solution stirred for a further 30 min.
  2. washwashed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 10% diethyl ether/hexane

Sources & evidence

ORD record
ord-31f2422a078d495bbb3b0381a2aada50
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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