N-Formylmorpholine → HCID 16110745, compound

HRID 404864Notes

Reaction equation

HRID 404864 reaction equation
C([Li])CCC.[CH:6]([O:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[CH:12][CH:11]=1)([CH3:8])[CH3:7].[CH:22](N1CCOCC1)=[O:23]>O1CCCC1>[CH:6]([O:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][C:15]2[S:16][C:17]([CH:22]=[O:23])=[CH:18][N:19]=2)=[CH:12][CH:11]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 20417N-FormylmorpholineHCID 670969222-(4-Isopropoxyphenoxy)-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 16110745HCID 16110745, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butyl lithium (20 mL, of 2.5M solution, 0.05 mol) at −78° C. over 15 minutes was added to a solution of Example 1B (11.8 g, 0.05 mol) in dry tetrahydrofuran. After one hour at the same temperature, formylmorpholine (5.8 g, 0.05 mol) was added drop wise and the mixture was stirred for 4 hours and then quenched with sat. NH4Cl. The aqueous layer was extracted with ethyl acetate and the organic phase washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated and purified on silica gel (5˜35% ethyl acetate in hexane) to give 13.2 g of product as a yellow oil, 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (d, J=5.88 Hz, 6H) 4.46-4.61 (m, 1H) 6.88-6.98 (m, 2H) 7.12-7.23 (m, 2H) 7.93 (s, 1H) 9.83 (s, 1H). MS (ESI), m/z 264.1 (M+H)+.

Workup

  1. customquenched with sat. NH4Cl
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe organic phase washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified on silica gel (5˜35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6a2283682ebf4b018be765d0151e6dcc
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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