N-Formylmorpholine → HCID 14995662, compound

HRID 1646964Notes

Reaction equation

HRID 1646964 reaction equation
C([Li])CCC.Br[C:7]1[C:15]2[O:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[CH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[CH:24](N1CCOCC1)=[O:25].[Cl-].[NH4+]>O1CCCC1>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[O:14][C:15]3[C:7]([CH:24]=[O:25])=[CH:8][CH:9]=[CH:10][C:11]=3[CH:12]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 20417N-FormylmorpholineHCID 25517Ammonium ChlorideHCID 14995661HCID 14995661, compoundHCID 178418339Butyllithium

Product 1

HCID 14995662HCID 14995662, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

83 ml of butyllithium were added at -70° C. to a mixture of 36.4 g of the product of Step B and 100 ml of tetrahydrofuran and the mixture was stirred for one hour at -60° C., 24.2 ml of N-formyl morpholine in 50 ml of tetrahydrofuran were added and the reaction mixture was stirred for 16 hours at -60° C. Ammonium chloride was added and the two phases were decanted. Extraction was carried out with ethyl acetate, followed by drying and concentrating to obtain 35.12 g of product which was purified by chromatography on silica, eluting with a hexane - ethyl acetate mixture (9-1) to obtain 13.8 g of the desired product.

Workup

  1. stirringthe reaction mixture was stirred for 16 hours at -60° C
  2. customthe two phases were decanted
  3. extractionExtraction
  4. customby drying
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-4f7ff7a05d544263b2f4900d26e1bd78
Source dataset
uspto-grants-1993_01
Patent number
US05182295

Reaction notes

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