Water → HCID 22671994, compound

HRID 1006549Notes

Reaction equation

HRID 1006549 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[N:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:16]([CH3:18])[CH3:17].C([Li])CCC.[CH:28](=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32].O>C1COCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[N:15]([S:19]([CH2:22][CH:28]([OH:33])[CH2:29][CH2:30][CH2:31][CH3:32])(=[O:21])=[O:20])[CH:16]([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 8063PentanalHCID 23378642HCID 23378642, compoundHCID 178418339Butyllithium

Product 1

HCID 22671994HCID 22671994, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of 2-(N-isopropyl-methylsulfonylamino)-5-trifluoromethyl-phenyl methoxymethyl ether (135 mg; prepared in Reference Example 30.) in THF (3.0 ml), hexamethylphosphoramide (420 μl) was added in a stream of argon. At −78° C., n-butyl lithium (742 μl) was added dropwise thereto. The mixture was stirred for 1.5 hours. To the mixture, a solution of valeraldehyde (102 mg) in THF (1.0 ml) was added dropwise. The mixture was stirred for 30 minutes. To the reaction mixture, water was added. The mixture was extracted with ethyl acetate, washed, dried over and concentrated with the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt=4:1) to give the title compound (69 mg) having the following physical data.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed
  4. customdried over and
  5. concentrationconcentrated with the reduced pressure
  6. customThe residue was purified on silica gel column chromatography (hexane:AcOEt=4:1)

Sources & evidence

ORD record
ord-cb98667288d84b5190064b38ccda73bd
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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