Sodium hydride → Tributyl-cyclobutoxymethyl-tin

HRID 1358312Notes

Reaction equation

HRID 1358312 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].I[CH2:9][Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14]>C1COCC1>[CH2:19]([Sn:10]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][O:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 10862926Tributyl(iodomethyl)stannane

Product 1

HCID 22273693Tributyl-cyclobutoxymethyl-tinYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.3 g of cyclobutanol in 60 mL of dry THF was added 624 mg of 98% sodium hydride. After stirring 2 h, 5.6 g of iodomethyl tributyltin (prepared as described by Seitz et al 1983 Synthetic Comm. 13 129) was added and the reaction mixture was stirred at room temperature for 48 h, and then poured onto water and extracted with hexanes. The extracts were washed with brine, dried and evaporated to a crude product that was purified by flash chromatography (hexanes then 67% ethyl acetate/hexanes eluents) to afford 1.64 g of tributyl (cyclobutyloxymethyl)tin as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 48 h
  2. additionpoured onto water
  3. extractionextracted with hexanes
  4. washThe extracts were washed with brine
  5. customdried
  6. customevaporated to a crude product that
  7. customwas purified by flash chromatography (hexanes

Sources & evidence

ORD record
ord-761d38459f4f42cca98c3831edafba20
Source dataset
uspto-grants-2003_07
Patent number
US06596729B2

Reaction notes

Loading…