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Potassium Carbonate → (3RS,4RS)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-4-[4-(5-(4,4,5,5,5-pentafluoropentylsulfonyl)pentyloxy)phenyl]thiochroman

HRID 1859343
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HRID 1859343 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7]([CH2:10][CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])(=[O:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[OH:44][C:45]1[CH:50]=[CH:49][C:48]([CH:51]2[C:60]3[C:55](=[CH:56][C:57]([O:61][CH2:62][O:63][CH3:64])=[CH:58][CH:59]=3)[S:54][CH2:53][C:52]2([C:66]2[CH:71]=[CH:70][C:69]([O:72][CH2:73][O:74][CH3:75])=[CH:68][CH:67]=2)[CH3:65])=[CH:47][CH:46]=1>O.C1C=CC=CC=1.CN(C)C=O>[CH3:64][O:63][CH2:62][O:61][C:57]1[CH:56]=[C:55]2[C:60]([CH:51]([C:48]3[CH:47]=[CH:46][C:45]([O:44][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7]([CH2:10][CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])(=[O:9])=[O:8])=[CH:50][CH:49]=3)[C:52]([C:66]3[CH:71]=[CH:70][C:69]([O:72][CH2:73][O:74][CH3:75])=[CH:68][CH:67]=3)([CH3:65])[CH2:53][S:54]2)=[CH:59][CH:58]=1
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 22123581(3RS,4RS)-4-(4-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochromanHCID 221235825-(5-Chloropentylsulfonyl)-1,1,1,2,2-pentafluoropentane

생성물 1

HCID 22123606(3RS,4RS)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-4-[4-(5-(4,4,5,5,5-pentafluoropentylsulfonyl)pentyloxy)phenyl]thiochroman
수율 67%

시약·촉매·용매 2

HCID 962Water용매HCID 19608675Benzene dimethylformamide용매

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온도
100 °C

실험 절차

5-(5-Chloropentylsulfonyl)-1,1,1,2,2-pentafluoropentane (27 mg, 0.082 mmol), potassium carbonate (34 mg, 0.25 mmol) and 18-crown-6 (21 mg, 0.08 mmol) were added to benzene-dimethylformamide (1:1) solution (2 ml) of (3RS,4RS)-4-(4-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman (37 mg, 0.082 mmol) and then stirred for 8 hours at 100° C. under argon atmosphere. After adding water, the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified using silica gel plate (ethyl acetate:hexane=1:2) to obtain 41 mg (yield: 67%) of the title compound.

후처리

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe crude product thus obtained
  7. customwas purified

출처 및 근거

ORD 기록
ord-a4c262bb8eb34d24abf42c2a6b15d88e
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06153768

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