Tetrahydrofuran → HCID 21501736, compound

HRID 1288360Notes

Reaction equation

HRID 1288360 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].O1CCCC1.[CH2:20]([S:24]([CH2:27][Li])(=[O:26])=[O:25])[CH2:21][CH2:22][CH3:23].[Cl-].[NH4+]>[Hg].CCCCCC.O1CCCC1>[CH2:20]([S:24]([CH2:27][Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:1][CH2:2][CH2:3][CH3:4])(=[O:26])=[O:25])[CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 15096Tributyltin Chloride2×HCID 25517Ammonium ChlorideHCID 178506887HCID 178506887, compound

Product 1

HCID 21501736HCID 21501736, compound

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

A 250-ml, three-necked flask fitted with a stirrer, a dropping funnel, and a thermometer was swept thoroughly with argon and maintained in an air-free condition by a mercury-filled trap. The flask was charged with 27 ml. of tri-n-butyltin chloride dissolved in 50 ml. of tetrahydrofuran (THF). To the solution of tributyltin chloride was added dropwise with stirring 100 ml. of an approximately one-molar solution of (butylsulfonyl-methyl)lithium in a hexane-THF mixture. The temperature was held at -10° C to 10° C during the addition which required 15 minutes. The reaction mixture was then agitated by stirring at room temperature for 2 hours. The reaction mixture was hydrolyzed by pouring into aqueous one-molar ammonium chloride. Extraction from the hydrolyzate with ether solvent and purification by distillation yielded the desired product (butylsulfonylmethyl)-tributyltin. The product, a colorless liquid, had a boiling point of 161°-165° C/0.1 mm. Hg. Analysis gave 48.4% Carbon and 9.2% Hydrogen compared to the calculated values, respectively, of 48.0% and 9.0%. Infrared and proton nuclear magnetic resonance spectral analyses confirmed the assigned structure.

Workup

  1. customA 250-ml, three-necked flask fitted with a stirrer, a dropping funnel
  2. additionfilled trap
  3. additionThe flask was charged with 27 ml
  4. additionThe temperature was held at -10° C to 10° C during the addition which required 15 minutes
  5. stirringThe reaction mixture was then agitated
  6. stirringby stirring at room temperature for 2 hours
  7. extractionExtraction from the hydrolyzate
  8. customwith ether solvent and purification
  9. distillationby distillation

Sources & evidence

ORD record
ord-a77221028c514be8a31be71df7bdc6bc
Source dataset
uspto-grants-1976_10
Patent number
US03988145

Reaction notes

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