Aluminium lithium hydride → 2-Methyl-3,6-di-tert-butyl-fluorene

HRID 1452935Notes

Reaction equation

HRID 1452935 reaction equation
Cl[CH2:2][C:3]1[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=3)[CH2:6][C:5]=2[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:2][C:3]1[C:15]([C:16]([CH3:18])([CH3:17])[CH3:19])=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=3)[CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 219826922-Chloromethyl-3,6-di-t-butylfluorene

Product 1

HCID 219826962-Methyl-3,6-di-tert-butyl-fluoreneYield 102.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloromethyl-3,6-di-t-butylfluorene (0.74 g, 2.26 mmol) in THF (15 ml) was added a small portion of LiAlH4 (129 mg, 3.39 mmol) under stirring and the mixture was refluxed for 5 hours. The reaction was quenched with water and NaOH and extracted with ether. The ether solution was evaporated under vacuum to give a white solid yield of 0.68 g. 1H NMR (CDCl3): δ 7.80 and 7.66 (each d, 1H, 4,5-H), 7.45 (d, 1H, J=8.1 Hz, H8), 7.31 (dd, 1H, J=8.1 Hz, J=1.5 Hz, H7), 7.14 (br s, 1H, 1H, H1), 3.69 (s, 2H, H9), 2.40 (s, 3H, Me), 1.41 (s, 18H, t-Bu).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customThe reaction was quenched with water and NaOH
  3. extractionextracted with ether
  4. customThe ether solution was evaporated under vacuum

Sources & evidence

ORD record
ord-caa2c4fa28d740a7a8030af2890eb5b2
Source dataset
uspto-grants-2009_01
Patent number
US07473813B2

Reaction notes

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