Water → HCID 66918669, compound

HRID 1367479Notes

Reaction equation

HRID 1367479 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10].[CH:11]1(OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15][CH:14]=[CH:13][CH2:12]1.O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH:14]1[CH2:13][CH:12]=[CH:11][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80599o-ChlorothiophenolHCID 357673HCID 357673, compound

Product 1

HCID 66918669HCID 66918669, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

NaH (316 mg, 55% in mineral oil, 7.24 mmol) was suspended in DMF (6 ml) and the suspension was cooled to 0° C. A solution of 2-chloro-thiophenol (880 ml, 97% purity, 7.55 mmol) in DMF (2 ml) was added dropwise. After stirring for 45 min at 0° C. a solution of toluene-4-sulfonic acid cyclopent-3-enyl ester (1500 mg, 6.29 mmol) in DMF (3 ml) was added dropwise and the reaction mixture was stirred at room temperature for 2 days. Water was added and the mixture was extracted 3 times with EtOAc. The combined organic layers were washed with water, saturated NaHCO3 solution and brine, dried over Na2OS4 and evaporated. The remaining brown oil was purified by silica gel chromatography (heptane/EtOAc 100:0-99:1) to obtain the title compound (1.047 g, 79%) as colorless liquid.

Workup

  1. additionwas added dropwise
  2. extractionthe mixture was extracted 3 times with EtOAc
  3. washThe combined organic layers were washed with water, saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2OS4
  5. customevaporated
  6. customThe remaining brown oil was purified by silica gel chromatography (heptane/EtOAc 100:0-99:1)

Sources & evidence

ORD record
ord-f2a008a51b2043f6a0f4796cddc43fce
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

Loading…