Water → HCID 22671994、化合物

HRID 1279614ノート

反応式

HRID 1279614 の反応式
[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]

参加物

7

反応物 4

HCID 962WaterHCID 8063PentanalHCID 23378642HCID 23378642、化合物HCID 178418339Butyllithium

生成物 1

HCID 22671994HCID 22671994、化合物収率 40.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 12679Hexamethylphosphoramide溶媒

実験手順

To a solution of 2-(N-isopropyl-methylsulfonylamino)-5-trifluoromethylphenyl 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.

後処理

  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)

出典と根拠

ORDレコード
ord-0216a91411a24593b9cd8c2bb763581f
出典データセット
uspto-grants-2002_09
特許番号
US06448290B1

反応ノート

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