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

HRID 362961노트

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HRID 362961 반응식
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

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 537589084-BenzylthiobenzaldehydeHCID 178478511HCID 178478511, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-10 °C

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-6c3c50818234425aa2ae8ed8e77986ce
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872117

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