Toluene → [5-(2,4-Dimethyl-3-pyridinyl)-2-(1-methylethyl)-1,4-cyclopentadien-1-yl]methanol

HRID 2423495Notes

Reaction equation

HRID 2423495 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[C:12]([C:13](OC)=[O:14])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH2:10][CH:9]=2)=[C:6]([CH3:20])[CH:5]=[CH:4][N:3]=1.[H-].C([Al+]C(C)C)(C)C.C1(C)C=CC=CC=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[CH3:1][C:2]1[C:7]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH:17]([CH3:18])[CH3:19])[CH2:10][CH:9]=2)=[C:6]([CH3:20])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 9357Potassium Sodium TartrateHCID 21896610Diisopropylaluminium hydride2×HCID 67243712Methyl 5-(2,4-dimethyl-3-pyridinyl)-2-(1-methylethyl)-1,4-cyclopentadiene-1-carboxylate

Product 1

HCID 67242851[5-(2,4-Dimethyl-3-pyridinyl)-2-(1-methylethyl)-1,4-cyclopentadien-1-yl]methanolYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-(2,4-dimethyl-3-pyridinyl)-2-(1-methylethyl)-1,4-cyclopentadiene-1-carboxylate (0.17 g, 0.62 mmol) in THF (1.7 mL) was stirred at 0° C. as a 1.5 M solution of diisopropylaluminum hydride in toluene (0.88 mL, 1.32 mmol) was added. The solution was allowed to warm to room temperature and stir overnight. The solution was then cooled to 0° C. before adding additional portion of diisopropylaluminum hydride in toluene (0.88 mL, 1.32 mmol). The solution was allowed to stir overnight before the addition a 10% aqueous solution of Rochelle's salt. The solution was then allowed to stir overnight. The solution was extracted with ethyl acetate and the organic layer was dried with MgSO4, filtered and concentrated. The residue was purified by chromatography (silica gel, dichloromethane to 19:1 dichloromethane:methanol) to yield [5-(2,4-dimethyl-3-pyridinyl)-2-(1-methylethyl)-1,4-cyclopentadien-1-yl]methanol (98 mg, 64%). 1H NMR (400 MHz, DMSO-d6): δ 8.37 (d, J=5 Hz, 1H), 7.18 (d, J=5 Hz, 1H), 4.87 (t, J=5 Hz, 1H), 4.04 (d, J=5 Hz, 2H), 3.34 (septet, J=7 Hz, overlapping water), 2.18 (s, 3H), 2.02 (s, 3H), 1.30 (d, J=7 Hz, 6H).

Workup

  1. additionwas added
  2. temperatureThe solution was then cooled to 0° C.
  3. stirringto stir overnight
  4. extractionThe solution was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (silica gel, dichloromethane to 19:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-f3aa3c6476fb48f7b29d7652e5539a75
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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