Water → HCID 10716721, compound

HRID 1379794Notes

Reaction equation

HRID 1379794 reaction equation
[CH3:1][C:2]1[C:3]([S:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.ClC1C=C(C=CC=1)C(OO)=[O:33].[OH2:39]>C(Cl)Cl>[CH3:1][C:2]1[C:3]([S:16]([C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)(=[O:33])=[O:39])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 11794316HCID 11794316, compound2×

Product 1

HCID 10716721HCID 10716721, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 69 mg (0.18 mmol) of ethyl 4-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthylthio)benzoate (Compound 6) in 2.0 mL of methylene chloride was dropwise added a solution of 87 mg of m-chloroperoxybenzoic acid (0.27 mmol, 50-60%) in 2.0 mL of methylene chloride, and the resulting solution was stirred for 3 h. The reaction was diluted with water and extracted with methylene chloride (2×). The combined organic layers were dried (MgSO4), filtered, and the solvents removed in vacuo to give a white solid. The crude product was purified by flash chromatography on silica gel (9:l/hexane:ethyl acetate) to give the title compound as a white solid (51 mg, 94%):

Workup

  1. extractionextracted with methylene chloride (2×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvents removed in vacuo
  5. customto give a white solid
  6. customThe crude product was purified by flash chromatography on silica gel (9:l/hexane:ethyl acetate)

Sources & evidence

ORD record
ord-3f46c0de889e4a33a2827c45267a031e
Source dataset
uspto-grants-1997_09
Patent number
US05672710

Reaction notes

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