Tributyltin Chloride → HCID 18446905, compound

HRID 1268917Notes

Reaction equation

HRID 1268917 reaction equation
Br[C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:4][C:3]=1[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.[Li]C(C)(C)C.[CH2:32]([Sn:36](Cl)([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH3:35].C(=O)([O-])O.[Na+]>C1COCC1>[C:15]1([C:5]2[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:2]([Sn:36]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:32][CH2:33][CH2:34][CH3:35])=[C:3]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[N:4]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 516892Sodium BicarbonateHCID 18446907HCID 18446907, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 18446905HCID 18446905, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 2 (13.4 g, 31.2 mmol) in THF (200 ml) at −78° C. was added dropwise tBuLi (22 ml, 1.7M, 38 mmol). After 25 minutes tributyltin chloride (12.37 g, 10.3 ml, 38 mmol) was added dropwise and the mixture was then allowed to reach room temperature overnight. The reaction was then poured into a saturated solution of sodium hydrogen carbonate and washed several times with diethyl ether. The combined organic layers were dried (magnesium sulphate), concentrated in vacuo and the residue purified by silica gel chromatography, eluting with a 0.5:4.5:45:50 mixture of 0.88 ammonia solution:methanol:hexane:diethyl ether to give the title compound (18.5 g, 93%) as a brown viscous oil; MS(AP+) m/e 641/643/644[M+H]+.

Workup

  1. washwashed several times with diethyl ether
  2. dry with materialThe combined organic layers were dried (magnesium sulphate)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by silica gel chromatography
  5. washeluting with a 0.5:4.5:45:50 mixture of 0.88 ammonia solution

Sources & evidence

ORD record
ord-0ed7a4b746ac4ce0b08ad207ec336f31
Source dataset
uspto-grants-2007_04
Patent number
US07199137B2

Reaction notes

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