Tetrahydrofuran → HCID 131734530, 화합물

HRID 591530노트

반응식

HRID 591530 반응식
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14]O)[CH2:11][O:12][C:8]=2[CH:7]=1.C1COCC1.CS(Cl)(=O)=O.[C:33](=[S:36])([O-:35])[CH3:34].[K+]>CN(C=O)C.CCN(CC)CC>[C:33](=[O:35])([S:36][CH2:14][CH2:13][C@H:10]1[C:9]2[CH:16]=[CH:17][C:6]([O:5][CH2:4][C:3]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:2]=3[Cl:1])=[CH:7][C:8]=2[O:12][CH2:11]1)[CH3:34]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 23670855Potassium ethanethioateHCID 89767792HCID 89767792, 화합물

생성물 1

HCID 131734530HCID 131734530, 화합물수율 71.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a mixture of 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanol (678 mg) and THF (dry) (20 mL) were added methanesulfonyl chloride (0.310 mL) and Et3N (0.279 mL). The mixture was stirred at room temperature for 30 min. And then DMF (dry) (20.00 mL) and potassium ethanethioate (228 mg) were added to the mixture. The volatiles (THF) were removed by evaporation. The resulting mixture was stirred at 70° C. for 2 h. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (570 mg).

후처리

  1. customThe volatiles (THF) were removed by evaporation
  2. stirringThe resulting mixture was stirred at 70° C. for 2 h
  3. additionThe mixture was poured into water
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

출처 및 근거

ORD 기록
ord-dc23030cdd664d9092448964fe8fbee6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238639B2

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