Hydrochloric Acid → 1-(4-Benzylthiophenyl)-2-(2-chloroethoxy)ethanol

HRID 862514ノート

反応式

HRID 862514 の反応式
C([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[S:13])=[CH:10][CH:9]=1)C1C=CC=CC=1.[Cl:16][CH2:17][CH2:18][O:19][CH2:20][Mg]Cl.[Cl-].[NH4+].Cl.C([O:29][CH2:30][CH3:31])(=O)C>O1CCCC1>[CH2:12]([S:13][C:8]1[CH:15]=[CH:14][C:31]([CH:30]([OH:29])[CH2:20][O:19][CH2:18][CH2:17][Cl:16])=[CH:10][CH:9]=1)[C:11]1[CH:10]=[CH:9][CH:8]=[CH:15][CH:14]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 537589084-BenzylthiobenzaldehydeHCID 178478511HCID 178478511、化合物

生成物 1

HCID 537562141-(4-Benzylthiophenyl)-2-(2-chloroethoxy)ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

1.19 g of 4-benzylthiobenzaldehyde was dissolved in 20 ml of tetrahydrofuran. The solution was cooled to -10° C. Thereto was dropwise added 10 ml of a tetrahydrofuran solution containing 2M of 2-chloroethoxymethylmagnesium chloride in 10 minutes. The resulting mixture was stirred for 1 hour with ice cooling. The reaction mixture was added to a mixture of 50 ml of ice water, 50 ml of ethyl acetate and 1 g of ammonium chloride. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography [eluant: toluene/ethyl acetate=20/1] to obtain 1.34 g of 1-(4-benzylthiophenyl)-2-(2-chloroethoxy)ethanol.

後処理

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography [eluant: toluene/ethyl acetate=20/1]

出典と根拠

ORDレコード
ord-dd99786adc3b45d9845fc668ecb0ef3b
出典データセット
uspto-grants-1998_02
特許番号
US05719150

反応ノート

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