N-Formylmorpholine → HCID 87833322, compound

HRID 404920Notes

Reaction equation

HRID 404920 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([CH3:16])[CH3:15])=[CH:9][N:8]=2)=[CH:4][CH:3]=1.C([Li])CCC.[CH:24](N1CCOCC1)=[O:25]>O1CCCC1>[CH:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:17]=[CH:18][C:2]([CH:24]=[O:25])=[CH:3][CH:4]=2)=[N:8][CH:9]=1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 20417N-FormylmorpholineHCID 69144624HCID 69144624, compoundHCID 178418339Butyllithium

Product 1

HCID 87833322HCID 87833322, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 69B (1.00 g, 3.25 mmol) in tetrahydrofuran (10 mL) was added n-butyl lithium (2.5 M in hexanes, 1.35 mL, 3.38 mmol) at −78° C. The mixture was stirred for 30 minutes, and then 4-formylmorpholine (380 μL) 3.80 mmol) was added. The mixture was stirred for 30 minutes and warmed to room temperature before quenching with water. The aqueous layer was extracted with ether (1×). The ether layer was washed with brine (1×), dried over MgSO4 and concentrated to give the title compound as colorless viscous oil.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. custombefore quenching with water
  3. extractionThe aqueous layer was extracted with ether (1×)
  4. washThe ether layer was washed with brine (1×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-06d7db6306454ed38abaf7dbd8ebd8a8
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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