Diethyl Ether → Stannane, (4-chlorophenyl)trimethyl-
Reaction equation
[CH3:1][Sn:2](Cl)([CH3:4])[CH3:3].C1COCC1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Mg]Br)=[CH:14][CH:13]=1.CCOCC>>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Sn:2]([CH3:4])([CH3:3])[CH3:1])=[CH:14][CH:13]=1Participants
Procedure
To a 1M solution of trimethyltin chloride in THF (92 ml, 92 mmol) was slowly added a 1M solution of 4-chlorophenylmagnesium bromide in Et2O (92 ml, 92 mmol) over a 40 min period at −10° C. so that the temperature never exceed 0° C. After the addition, the cooling bath was removed and the resulting suspension was stirred at RT for 1 h. A saturated aqueous solution of NH4Cl (14 ml) was added followed by water until complete dissolution of the precipitate. The mixture was transferred into a separating funnel and extracted with Et2O (3×). The combined organic fractions were dried over Na2SO4: filtered and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; isocratic elution with cyclohexane) to yield the title compound (24.47 g, 89 mmol, 97%) as a colorless oil. TLC: RF=0.76 (cyclohexane AcOEt 95:5); HPLC: AtRet=3.25 min; 1H NMR (400 MHz, CDCl3): 0.31 (s, 9H) 7.32-7.36 (m, 2H) 7.41-7.45 (m, 2H).
Workup
- additionAfter the addition
- customthe cooling bath was removed
- additionA saturated aqueous solution of NH4Cl (14 ml) was added
- dissolutionfollowed by water until complete dissolution of the precipitate
- customThe mixture was transferred into a separating funnel
- extractionextracted with Et2O (3×)
- dry with materialThe combined organic fractions were dried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
- customThe resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; isocratic elution with cyclohexane)
Sources & evidence
- ORD record
- ord-bc42bc2bf50b4ca28908687ad886b946
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073898B2
Reaction notes
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