Iodine → HCID 86745717, compound

HRID 374268Notes

Reaction equation

HRID 374268 reaction equation
II.[OH:3][CH2:4]/[CH:5]=[C:6](/[CH2:8][CH2:9]/[CH:10]=[C:11](/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])\[CH3:12])\[CH3:7].[CH2:19]([Sn:23]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:24]I)[CH2:20][CH2:21][CH3:22]>O1CCCC1>[CH2:30]([Sn:23]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:24][O:3][CH2:4][CH:5]=[C:6]([CH3:7])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 807IodineHCID 445070FarnesolHCID 10862926Tributyl(iodomethyl)stannane

Product 1

HCID 86745717HCID 86745717, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1.15 g (10.0 mmol) of 35% KH in mineral oil was washed with three 5 mL portions of dry hexane and suspended in 15 mL of dry tetrahydrofuran (THF) under argon. A solution of 242 mg (0.95 mmol) of iodine in 10 mL of THF was added over 50 minutes and the reaction was allowed to stir for an additional 40 minutes at room temperature to give a white suspension. (E,E)-Farnesol (1.5 g, 6.75 mmol) in 10 mL of THF was added dropwise over 15 minutes, and after 75 minutes, a solution of 2.43 g (5.64 mmol) of tributyl(iodomethyl)tin was added rapidly in 6 mL of THF. The mixture was stirred for three hours and carefully quenched with methanol. Upon dilution with diethyl ether, the organic layer was washed with water and brine, dried (MgSO4) and evaporated to give 3.21 g of a pale yellow liquid. The crude material was chromatographed on 720 g of silica gel eluted with 0.5:99.5 diethyl ether: petroleum ether, and the impure fractions were further purified on 150 g of silica gel eluted with 0.33:99.67 diethyl ether:petroleum ether to provide a total of 2.09 g (71%) of pure title stannane as a colorless liquid.

Workup

  1. washA 1.15 g (10.0 mmol) of 35% KH in mineral oil was washed with three 5 mL portions of dry hexane
  2. customto give a white suspension
  3. waitafter 75 minutes
  4. stirringThe mixture was stirred for three hours
  5. customcarefully quenched with methanol
  6. washUpon dilution with diethyl ether, the organic layer was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-a87b08887cd74f6282136bf20e43b6eb
Source dataset
uspto-grants-1992_11
Patent number
US05166386

Reaction notes

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