Indene → HCID 23368005, compound

HRID 1902163Notes

Reaction equation

HRID 1902163 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].I[CH2:21][CH2:22][CH:23]1[O:30][CH2:29][CH2:28][O:27][CH:24]1[CH2:25]I>C1COCC1>[CH2:29]1[CH2:28][O:27][C:23]2([CH2:24][CH2:25][C:1]3([C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)[CH2:21][CH2:22]2)[O:30]1

Participants

5

Reactant 3

HCID 7219IndeneHCID 2733832Lithium HexamethyldisilazideHCID 70343545HCID 70343545, compound

Product 1

HCID 23368005HCID 23368005, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of indene (0.84 g, 7.3 mmol) in THF at 0° C. was added lithium bis(trimethylsilyl)amide (14.6 ml, 14.6 mmol). After 30 minutes of stirring the anion was cannulated into a solution of 1,5-diiodo-3-ethylenedioxypentane (2.79 g, 7.3 mmol) prepared as described in J. Am. Chem. Soc. 1990, 9001-9003). The reaction mixture was stirred for 1 h and then warmed to room temperature over night. The reaction mixture was concentrated and purified by flash chromatography (silica gel, hexane/ethyl acetate 10:1) to give the title compound (1.2 g, 4.9 mmol).

Workup

  1. customprepared
  2. stirringThe reaction mixture was stirred for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by flash chromatography (silica gel, hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-3212858df9644f06ae18e393aa43d32d
Source dataset
uspto-grants-1996_11
Patent number
US05578593

Reaction notes

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