Ethanethiol → HCID 22718074, compound

HRID 460456Notes

Reaction equation

HRID 460456 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:45]=[CH:44][C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:46]3[CH:51]=[CH:50][C:49]([O:52]C)=[CH:48][CH:47]=3)[S:8][C:7]=2[CH:54]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.O1CCCC1>ClCCl.O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:45]=[CH:44][C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:39])([F:40])[F:41])([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:46]3[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=3)[S:8][C:7]=2[CH:54]=1

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 8028TetrahydrofuranHCID 6451240Aluminum(III) ChlorideHCID 22718069HCID 22718069, compound

Product 1

HCID 22718074HCID 22718074, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Diethyl 2-[5-[4-[(6-methoxy-2-(4-methoxyphenyl)benzo-[b]thiophen-3-yl)carbonyl]phenoxy]pentyl]-2-(4,4,5,5,5-pentafluoropentyl)malonate (1.58 g, 2.03 mmol) was dissolved in dichloromethane (40 ml), and aluminum chloride (1.62 g, 12.2 mmol) and ethanethiol (0.25 ml, 10.15 mmol) were added to the resulting solution followed by stirring for 1.5 hours at room temperature. After the reaction mixture was cooled to 0° C., tetrahydrofuran (30 ml) was slowly added to the reaction mixture, which was then diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/2) to give diethyl 2-[5-[4-[(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)carbonyl]phenoxy]pentyl]-2-(4,4,5,5,5-pentafluoropentyl)malonate (1.2 g, Yield 79%) as a brown foam.

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-890e67800e8d4e5ea2103a0f07af5185
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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