Dichloromethane → HCID 19068283, compound

HRID 1957683Notes

Reaction equation

HRID 1957683 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([S:19][CH2:20][C:21]4[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.ClCCl.ClC1C=CC=C(C(OO)=[O:42])C=1>O>[C:1]12([C:11]3[CH:12]=[C:13]([S:19]([CH2:20][C:21]4[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=4)=[O:42])[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 19068287HCID 19068287, compound

Product 1

HCID 19068283HCID 19068283, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

844 mg (2 mmol) of methyl 4-[3-(1-adamantyl)-4-methoxyphenylthiomethyl]benzoate and 20 ml of dichloromethane were introduced into a round-bottomed flask and 386 mg (1.9 mmol) of meta-chloroperbenzoic acid were added. The reaction medium was stirred at room temperature for two hours and was then poured into water and extracted with dichloromethane. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a column of silica, eluted with a mixture of dichloromethane and ethyl ether (90/10). After evaporation of the solvents, 270 mg (30%) of the expected ester, having a melting point of 121°-2° C., were recovered.

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by chromatography on a column of silica
  6. washeluted with a mixture of dichloromethane and ethyl ether (90/10)
  7. customAfter evaporation of the solvents, 270 mg (30%) of the expected ester
  8. customwere recovered

Sources & evidence

ORD record
ord-603022476b3045a695edb0663f153ada
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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