Triethylamine → HCID 86752493, compound

HRID 1600381Notes

Reaction equation

HRID 1600381 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][O:10][C@H:11]1[CH2:15][C@H:14](O)[CH:13]=[CH:12]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(N(CC)CC)C.[C:24]1(C)[C:25]([S:30](Cl)=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1>C(Cl)Cl>[CH2:1]([O:3][P:4]([CH2:9][O:10][C@H:11]1[CH2:15][C@H:14]([S:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:24]=2)=[O:31])[CH:13]=[CH:12]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13902623Toluenesulfinyl chlorideHCID 86752492HCID 86752492, compound

Product 1

HCID 86752493HCID 86752493, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Trans-1-diethylphosphonomethoxycyclopent-2-en-4-ol (0.4 g; 1.6 mmol) was dissolved in CH2Cl2 (6 mL) and cooled to 0° C. in an icebath under a nitrogen atmosphere. Triethylamine (0.3 g; 2.9 mmol) was then added followed by a solution of toluenesulfinyl chloride (0.4 g, 2.9 mmol)in CH2Cl2 (2 mL). The reaction mixture was stirred at 0° C. for 1 hr. The ice bath was removed and the reaction mixture concentrated in vacuo. The residual oil was purified by flash column chromotography with 2% methanol/98% dichloromethane as eluent. The product(0.54 g; 87%) was isolated as a colorless oil.

Workup

  1. customThe ice bath was removed
  2. concentrationthe reaction mixture concentrated in vacuo
  3. customThe residual oil was purified by flash column chromotography with 2% methanol/98% dichloromethane as eluent
  4. customThe product(0.54 g; 87%) was isolated as a colorless oil

Sources & evidence

ORD record
ord-4a6e008e1c9c42c399de059ff9ad842d
Source dataset
uspto-grants-1998_04
Patent number
US05744600

Reaction notes

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