Ammonium Chloride → alpha-(1-Ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcohol

HRID 1721935ノート

反応式

HRID 1721935 の反応式
C([Li])CCC.[CH2:6]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[CH3:7].[Cl:15][C:16]1[C:23]([Cl:24])=[C:22]([O:25][CH3:26])[CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].[Cl-].[NH4+]>CCCCCC.O1CCCC1.O>[CH2:6]([O:8][CH2:9][N:10]1[C:14]([CH:18]([OH:19])[C:17]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[C:23]([Cl:24])[C:16]=2[Cl:15])=[CH:13][CH:12]=[N:11]1)[CH3:7]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 130156892,3-Dichloro-4-methoxybenzaldehydeHCID 157143991-(ethoxymethyl)-1H-pyrazoleHCID 178418339Butyllithium

生成物 1

HCID 14622784alpha-(1-Ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcohol収率 81.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

4.13 ml of 1.6M n-butyl lithium in hexane are added dropwise to a tetrahydrfuran solution of 0.76 g of 1-ethoxymethylpyrazole at -60° C. under argon gas atmosphere. the mixture is stirred at -63° to -50° C. for 1 hour. A solution of 1.23 g of 2,3-dichloro-4-methoxybenzaldehyde in tetrahydrofuran is added to the mixture, and the mixture is stirred at -50° C. to room temperature for 1 hour. An aqueous saturated ammonium chloride solution and water are added to the mixture under ice-cooling and the mixture is concentrated to remove tetrahydrofuran. The residual aqueous layer is extracted with ethyl acetate and the extract is washed with water, dried and evaporated to give colorless crystals, which are then washed with isopropyl ether and dried to give 1.62 g of α-(1-ethoxymethyl-5-pyrazolyl)-2,3-dichloro-4-methoxy-benzylalcohol.

後処理

  1. stirringthe mixture is stirred at -50° C. to room temperature for 1 hour
  2. temperaturecooling
  3. concentrationthe mixture is concentrated
  4. customto remove tetrahydrofuran
  5. extractionThe residual aqueous layer is extracted with ethyl acetate
  6. washthe extract is washed with water
  7. customdried
  8. customevaporated
  9. customto give colorless crystals, which
  10. washare then washed with isopropyl ether
  11. customdried

出典と根拠

ORDレコード
ord-80735a99aa4444a89e563646f5f0c8f6
出典データセット
uspto-grants-1989_08
特許番号
US04853404

反応ノート

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