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 1859343Notes

Reaction equation

HRID 1859343 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19608675Benzene dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a4c262bb8eb34d24abf42c2a6b15d88e
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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