p-Toluenesulfonic acid → HCID 22672749, compound

HRID 726115Notes

Reaction equation

HRID 726115 reaction equation
[C:1]1(C)C=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(N(CC)CC)C.C(=O)(O)[O-:28].[Na+]>O1C=CCCC1.O1CCCC1>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH:5]2[CH2:4][CH2:3][CH2:2][CH2:1][O:28]2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 660494-BromothiophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 22672749HCID 22672749, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80803,4-dihydro-2H-pyranSolvent

Procedure

2.3 mg of p-toluene sulfonic acid were added to a solution of 1 g of 4-bromo thiophenol in 1 ml of 3,4-dihydro-[2H]-pyran and 1 ml of tetrahydrofuran and the mixture was stirred for 20 hours at ambient temperature. 0.1 ml of triethylamine were added and the mixture was poured into a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried and evaporated to dryness under reduced pressure. The 1,603 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 97.5-2.5) to obtain 1.246 g of the expected product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customThe 1,603 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 97.5-2.5)

Sources & evidence

ORD record
ord-3053b902855945cc8be1d9a908feebd0
Source dataset
uspto-grants-1998_01
Patent number
US05707982

Reaction notes

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