Trimethyltin chloride → 1,1-Dimethylethyl N-[2-(trimethylstannyl)-3-thienyl]carbamate

HRID 712073Notes

Reaction equation

HRID 712073 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].C([Li])CCC.Cl[Sn:21]([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[CH3:22][Sn:21]([CH3:24])([CH3:23])[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 13164363tert-Butyl (2-bromothiophen-3-yl)carbamateHCID 178418339Butyllithium

Product 1

HCID 103612511,1-Dimethylethyl N-[2-(trimethylstannyl)-3-thienyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (2-bromo-3-thienyl)carbamate (4.81 g, 17.3 mmol) in THF (42 mL) was added 2.5 M n-butyllithium in hexanes (15.2 mL, 38.0 mmol) dropwise at −78° C. After stirring for 45 min, 1.0 M chlorotrimethylstannane in THF (19.0 mL, 19.0 mmol) was added. The resulting mixture was allowed to warm to room temperature. The reaction was quenched with brine (70 mL) and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give the desired product. 1H NMR (300 MHz, CDCl3) δ 7.49 (1H, d, J=4.8 Hz), 7.13 (1H, d, J=4.8 Hz), 6.39 (1H, brs), 1.50 (9H, s), 0.36 (9H, s) ppm.

Workup

  1. customThe reaction was quenched with brine (70 mL)
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-86e948aaa2f14f1fa17fdf2c65893e2a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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