Water → 2-(2-tert-Butyl-1H-tetrazol-5-yl)phenyltri-n-butylstannane

HRID 1886073Notes

Reaction equation

HRID 1886073 reaction equation
C([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2Br)=[N:8][N:7]=[N:6]1)(C)(C)C.[Li]C[CH2:19][CH2:20][CH3:21].[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].O.[CH2:37]1COCC1>>[C:20]([N:7]1[NH:6][N:5]=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Sn:26]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:23][CH2:24][CH3:25])[NH:8]1)([CH3:19])([CH3:21])[CH3:37]

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 15096Tributyltin Chloride2×HCID 218408841-tert-Butyl-5-(2-bromophenyl)-1H-tetrazoleHCID 178418339Butyllithium

Product 1

HCID 676965402-(2-tert-Butyl-1H-tetrazol-5-yl)phenyltri-n-butylstannaneYield 45%

Procedure

To a cooled (-78° C.) solution of 1-tert-butyl-5-(2-bromophenyl)-1H-tetrazole (12.3 g, 0.043 mol), prepared as described in Step 3 of the Example 3 alternative synthesis, in THF (80 mL) was added 1.6M nBuLi in hexanes (32.7 mL, 0.052 mol). After 1 h, tri-n-butyltin chloride (17.1 g, 0.052 mol) was added and stirring was continued for 3 h at -78° C. The mixture was warmed to room temperature and stirred for 18 h. Water was added and the mixture was extracted with ether. The combined extracts were washed with water, brine, dried (MgSO4), and concentrated to give a brown oil. Excess tri-n-butyltin chloride and remaining starting material were removed by distillation under high vacuum to give 9.6 g (45%) of product as a brown oil.

Workup

  1. customprepared
  2. waitwas continued for 3 h at -78° C
  3. stirringstirred for 18 h
  4. extractionthe mixture was extracted with ether
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customwere removed by distillation under high vacuum

Sources & evidence

ORD record
ord-f64163b983b44d439a5951449609b6f4
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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