Thiophenol → (E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

HRID 2368868Notes

Reaction equation

HRID 2368868 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:21]([CH3:22])=[CH:20][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)=[CH:7][C:6]=1[CH3:23].C1CCC(N=C=NC2CCCCC2)CC1.[C:39]1([SH:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:23])=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14](=[O:16])[S:45][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:20][C:21]=1[CH3:22]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 10868DicyclohexylcarbodiimideHCID 67262065(E)-3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid

Product 1

HCID 86672878(E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-3-[4-(methoxymethoxy)-3,5-dimethylstyryl]benzoic acid (0.1 g, 0.320 mmol) in DCM (5 mL) were added DCC (72.6 mg, 0.352 mmol), DMAP (7.9 mg, 0.064 mmol), and benzenethiol (65.7 μL, 0.640 mmol) at room temperature. The reaction mixture was stirred overnight (about 18 hours) and filtered through Celite. The filtrate was washed with 10% citric acid, brine, and dried with Na2SO4. The solution was filtered and concentrated. The compound was purified by column chromatography (9:1 Hexane:EtOAc) to afford (E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate in quantitative yield.

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with 10% citric acid, brine
  3. dry with materialdried with Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customThe compound was purified by column chromatography (9:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-208e80c956a5438cb63a2877faf503d5
Source dataset
uspto-grants-2014_04
Patent number
US08703815B2

Reaction notes

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