1,1,3,3-Tetrabutyl-1,3-diisothiocyanatodistannoxane → HCID 53691823, compound

HRID 483652Notes

Reaction equation

HRID 483652 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[C:24]([F:33])[CH2:25][O:26]C1CCCCO1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(N=C=S)O[Sn](CCCC)(CCCC)N=C=S)CCC>CO>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[C:24]([F:33])[CH2:25][OH:26])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 166879751,1,3,3-Tetrabutyl-1,3-diisothiocyanatodistannoxaneHCID 53929479HCID 53929479, compound

Product 1

HCID 53691823HCID 53691823, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The tetrahydropyranyl derivative prepared in 3C (2.26 g, 4.8 mmoles) was dissolved in methanol. Tetrabutyl-1,3-diisothiocyanatodistannoxane (30 mg) was added and the mixture was refluxed for 24 hrs. Methanol was evaporated under reduced pressure. The residue was dissolved in ether and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography on silicagel and elution with a 2:8 mixture of hexane and ethyl acetate afforded the alcohol as an oil (1.65 g, 92%).

Workup

  1. temperaturethe mixture was refluxed for 24 hrs
  2. customMethanol was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washFlash chromatography on silicagel and elution
  9. additionwith a 2:8 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-3cd2a0094a404788ac07294eb72aadac
Source dataset
uspto-grants-1993_07
Patent number
US05225429

Reaction notes

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