Tributyltin Chloride → HCID 58207969, compound

HRID 1958492Notes

Reaction equation

HRID 1958492 reaction equation
[Li+].CC([N-]C(C)C)C.[CH:9]([N:12]([C:20]1[S:21][CH:22]=[CH:23][N:24]=1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH3:10].[CH2:25]([Sn:29](Cl)([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]>C1COCC1>[CH:9]([N:12]([C:20]1[S:21][C:22]([Sn:29]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:23][N:24]=1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 2724682Lithium diisopropylamideHCID 58207984HCID 58207984, compound

Product 1

HCID 58207969HCID 58207969, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

LDA (0.55M 1.1 mmol, 2M) was added to a RBF containing THF (5 mL) cooled to −78° C. A solution of tert-butyl isopropyl(thiazol-2-yl)carbamate (242 mg, 1 mmol) in THF (5 mL) was added via cannula and the resulting solution stirred for 2 h at −78° C. Tributyltin chloride (0.27 mL, 1 mmol) was added and the reaction mixture allowed to slowly warm to room temperature then stirred overnight. The reaction mixture was then quenched with NH4Cl (2 mL, sat. aq.) and diluted with water. The mixture was then extracted with EtOAc (3×25 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The product was isolated via column chromatography (SiO2, 2% EtOAc/heptane) to afford the product (214 mg, 40% yield) as a colorless oil.

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringthen stirred overnight
  3. customThe reaction mixture was then quenched with NH4Cl (2 mL, sat. aq.)
  4. additiondiluted with water
  5. extractionThe mixture was then extracted with EtOAc (3×25 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product was isolated via column chromatography (SiO2, 2% EtOAc/heptane)

Sources & evidence

ORD record
ord-d2d387ebcd3442ad850fb82be8d9ca00
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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