Ethanethiol → 4-(2-carbethoxy-1-ethyl)-7-hydroxy-2-oxo-2H-1-Benzopyran

HRID 6238

반응식

HRID 6238 반응식
[Al+3].[Cl-].[Cl-].[Cl-].CCS.[C:8]([CH2:13][CH2:14][C:15]1[C:20]2[CH:21]=[CH:22][C:23]([O:25]C)=[CH:24][C:19]=2[O:18][C:17](=[O:27])[CH:16]=1)([O:10][CH2:11][CH3:12])=[O:9]>ClCCl>[C:8]([CH2:13][CH2:14][C:15]1[C:20]2[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:19]=2[O:18][C:17](=[O:27])[CH:16]=1)([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

5

반응물 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 867472394-(2-carbethoxy-1-ethyl)-7-methoxy-2-oxo-2H-1-Benzopyran

생성물 1

HCID 124771144-(2-carbethoxy-1-ethyl)-7-hydroxy-2-oxo-2H-1-Benzopyran수율 27.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 726 mg (5.4 mmol) of AlCl3 in 10 mL of dichloromethane at 0° C. was added 4 mL of EtSH. The suspension became a clear solution within seconds. Then, 298 mg (1.08 mmol) of 3 in 4 mL of dichloromethane was added, turning the yellow solution red in color. The ice bath was removed, and the reaction stirred to room temperature for 3 h. The solvents were removed in vacuo, and the residue thoroughly vacuum dried. The residue was extracted into EtOAc as much as possible, then the extract was flash chromatographed using 30/70 EtOAc/hexane. The long- and short-wave UV active band gave 76.7 mg (27%) of 4.

후처리

  1. customThe ice bath was removed
  2. customThe solvents were removed in vacuo
  3. customthe residue thoroughly vacuum dried
  4. extractionThe residue was extracted into EtOAc as much as possible, then the extract
  5. customchromatographed

출처 및 근거

ORD 기록
ord-4f75d89850dd4de3a07f2755539ba444
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247099

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