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

HRID 2423495ノート

反応式

HRID 2423495 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f3aa3c6476fb48f7b29d7652e5539a75
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

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