p-Toluenesulfonic acid monohydrate → HCID 18319598, compound

HRID 1699382Notes

Reaction equation

HRID 1699382 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([S:25][CH3:26])[C:19]=2[O:18][CH2:17][CH2:16][CH:15]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:26][S:25][C:24]1[C:19]2[O:18][CH2:17][CH2:16][C:15]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:14][C:20]=2[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18319506HCID 18319506, compound

Product 1

HCID 18319598HCID 18319598, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of p-toluenesulfonic acid monohydrate (109 mg) and ethyl 5-hydroxy-9-methylthio-2,3,4,5-tetrahydro-1-benzoxepin-4-carboxylate (cis and trans mixture, 1.62 g) in toluene (32 ml) was heated to reflux for 1.5 hours. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate, and evaporated in vacuo to give 1.60 g of crude product, which was purified by column chromatography on silica gel using a mixture of n-hexane and ethyl acetate (30:1) to afford ethyl 2,3-dihydro-9-methylthio-1-benzoxepin-4-carboxylate (1.30 g, colorless needles).

Workup

  1. temperatureto reflux for 1.5 hours
  2. washwashed successively with saturated aqueous sodium hydrogen carbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give 1.60 g of crude product, which
  6. customwas purified by column chromatography on silica gel using
  7. additiona mixture of n-hexane and ethyl acetate (30:1)

Sources & evidence

ORD record
ord-cbb39e4f3b904ca383d380c1d47ec6ca
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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