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Tributyltin Chloride → 5-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)-2-[tri(n-butyl)stannyl]furan

HRID 566392
Notes
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Reaction equation

HRID 566392 reaction equation
[CH3:1][C:2]12[CH2:9][O:8][C:5]([C:10]3[O:11][CH:12]=[CH:13][CH:14]=3)([O:6][CH2:7]1)[O:4][CH2:3]2.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>C1COCC1>[CH3:1][C:2]12[CH2:3][O:4][C:5]([C:10]3[O:11][C:12]([Sn:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:13][CH:14]=3)([O:6][CH2:7]1)[O:8][CH2:9]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 15096Tributyltin ChlorideHCID 226097422-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)furan

Product 1

HCID 226097085-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)-2-[tri(n-butyl)stannyl]furanYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)furan (2.0 g, 10.2 mmol) was dissolved in THF (20 ml) and the solution was cooled to −78° C. n-Buli (1.6M solution in hexanes, 7.7 ml, 12.32 mmol) was added and the mixture stirred at −78° C. for 30 min, allowed to warm to 0° C. for 20 min. and then recooled to −78° C. The tributyltin chloride (3.5 ml, 4.68 g, 14.4 mmol) was added and stirring was continued at −78° C. for 15 min. The mixture was allowed to warm gradually to room temperature and stirring continued for three days. The reaction was quenched by the addition of water, and extracted with ethyl acetate. This solution was washed with water, dried (MgSO4), and concentrated in vacuo to give the title compound as a yellow oil (4.7 g, 9.7 mmol, 95%); δH [2H6]DMSO 6.52 (1H,d), 6.38 (1H,d), 3.96 (6H,s), 0.77-1.63 (30H,m).

Workup

  1. additionwas added
  2. temperatureto warm to 0° C. for 20 min.
  3. customrecooled to −78° C
  4. stirringstirring
  5. waitwas continued at −78° C. for 15 min
  6. temperatureto warm gradually to room temperature
  7. stirringstirring
  8. waitcontinued for three days
  9. customThe reaction was quenched by the addition of water
  10. extractionextracted with ethyl acetate
  11. washThis solution was washed with water
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa73696acc7e4bb580ecbae151507658
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06174889B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes