Diethyl Ether → HCID 58909953, compound

HRID 1295956Notes

Reaction equation

HRID 1295956 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:19](=[O:21])[CH3:20])[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Cl:22]N1C(=O)CCC1=O.CCOCC>O1CCCC1.C(N(CC)CC)C>[Cl:22][CH2:20][C:19]([C:7]1[CH:8]=[C:9]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:10]([O:11][CH3:12])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:21]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 31398ChlorosuccinimideHCID 22929663HCID 22929663, compound

Product 1

HCID 58909953HCID 58909953, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

After dissolving 1-[3-(tert-butyl)-4-methoxy-5-morpholinophenyl]-1-ethanone (9.5 g) in tetrahydrofuran (60 ml), triethylamine (13 ml) and tert-butyl dimethylsilyltrifluoromethanesulfonate (9.8 ml) were added dropwise while cooling on ice. The reaction mixture was stirred for 30 minutes while cooling on ice and then N-chlorosuccinimide (5.3 g) was gradually added. After continuing to stir the reaction mixture for 30 minutes, ether (2 l) was added thereto and the resulting mixture was washed twice with water. The organic layer was dried over anhydrous magnesium sulfate and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (4.87 g) as light yellow crystals.

Workup

  1. additionwere added dropwise
  2. temperaturewhile cooling on ice
  3. temperaturewhile cooling on ice
  4. stirringto stir the reaction mixture for 30 minutes
  5. washthe resulting mixture was washed twice with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b391e01203fa4787bf8428e36568c91d
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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