Tributylstannane → HCID 22595773, compound

HRID 1358313Notes

Reaction equation

HRID 1358313 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([SnH:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].[CH:26]([O:29][CH2:30]Cl)([CH3:28])[CH3:27]>C1COCC1>[CH2:22]([Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:30][O:29][CH:26]([CH3:28])[CH3:27])[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 7912DiisopropylamineHCID 124317162-(Chloromethoxy)propaneHCID 178418339Butyllithium

Product 1

HCID 22595773HCID 22595773, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4.6 mL diisopropylamine in 40 mL of dry THF at −20° C. was added dropwise first 12.0 ml of 2.5 M butyllithium and then 8.1 ml of tributyltinhydride. After 10 min this solution was cooled to −78° C., and 3.25 g of chloromethyl isopropyl ether (Molina et al, 1982 Synthesis, 944) was added dropwise. After 10 min the cooling bath was removed and the reaction mixture was stirred at ambient temperature for 1.5 h. The mixture was poured onto water and extracted with hexanes and the extracts were dried over sodium sulfate and evaporated. The crude product was distilled (0.2 mm, 110-130° C.) to afford 7.8 g of tributyl (isopropoxymethyl)tin as a colorless liquid.

Workup

  1. customAfter 10 min the cooling bath was removed
  2. additionThe mixture was poured onto water
  3. extractionextracted with hexanes
  4. dry with materialthe extracts were dried over sodium sulfate
  5. customevaporated
  6. distillationThe crude product was distilled (0.2 mm, 110-130° C.)

Sources & evidence

ORD record
ord-3d6850fc8b13400ca50da5cf9e3bb37c
Source dataset
uspto-grants-2003_07
Patent number
US06596729B2

Reaction notes

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