Sodium hydride → Tributyl (cyclopropylmethoxymethyl)tin

HRID 1358311Notes

Reaction equation

HRID 1358311 reaction equation
[CH:1]1([CH2:4][OH:5])[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][CH2:4][CH:1]1[CH2:3][CH2:2]1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 10862926Tributyl(iodomethyl)stannane

Product 1

HCID 22273698Tributyl (cyclopropylmethoxymethyl)tinYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.15 g of cyclopropyl carbinol in 30 mL of dry THF was added 312 mg of 98% sodium hydride. After stirring 1 h, 2.8 g of iodomethyl tributyltin (prepared as described by Seitz et al, 1983 Synthetic Commun. 13, 129) was added and the reaction mixture was stirred at room temperature for 24 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 30% ethyl acetate/hexanes eluents) to afford 1.03 g of tributyl (cyclopropylmethoxymethyl)tin as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 24 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-4780205fe32b44a8af9eaade6b46c337
Source dataset
uspto-grants-2003_07
Patent number
US06596729B2

Reaction notes

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