N,N,N',N'-Tetramethylethylenediamine → 3,3-Dimethyl-1-(1-imidazolyl)-1-(3-methoxyphenyl)5-hexen-2-ol

HRID 359047Notes

Reaction equation

HRID 359047 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.CN(CCN(C)C)C.C([Li])CCC.CCCCCC.[CH3:34][C:35]([CH3:41])([CH2:38][CH:39]=[CH2:40])[CH:36]=[O:37]>C1COCC1>[CH3:34][C:35]([CH3:41])([CH2:38][CH:39]=[CH2:40])[CH:36]([OH:37])[CH:6]([N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)[C:5]1[CH:12]=[CH:13][CH:14]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 796362,2-Dimethylpent-4-enalHCID 122293911-(3-methoxy-benzyl)-1H-imidazoleHCID 178418244HCID 178418244, compound

Product 1

HCID 142303363,3-Dimethyl-1-(1-imidazolyl)-1-(3-methoxyphenyl)5-hexen-2-olYield 6.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.52 g (40 mmol) of 1-(3-methoxybenzyl)-imidazole and 4.65 g (40 mmol) of TMEDA in 80 ml of absolute THF were metallized using 53.5 ml of 1.5 molar n-butyllithium/hexane solution according to the procedure described in Example 19, and the product was reacted with 5.00 g of 90% purity (≅40 mmol) 2,2-dimethyl-4-pentenaldehyde. Work-up was effected analogously to that in Example 19. The extract residue (12.2 g) was chromatographed as described in Example 19 on a silica gel S/CH2Cl2 column (φ 3.5 cm, height 40 cm), and the combined fractions which contained the compound desired (amount 6.3 g) were subsequently chromatographed a second time on a silica gel S/CH2Cl2 column (φ 2.4 cm, height 88 cm). A group of fractions (2.5 g) from the second chromatography crystallized from a hexane/diisopropyl ether 3:1 solution. After isolation of the substance, 0.77 g (≅6.3% yield) of pure 3,3-dimethyl-1-(1-imidazolyl)-1-(3-methoxyphenyl)5-hexen-2-ol of melting point 83° C. were obtained. C18H24N2O2 (300.41) calculated: C 71.97 H 8.05 N 9.33% found: C 68.9 H 8.0 N 8.6%.

Workup

  1. customThe extract residue (12.2 g) was chromatographed
  2. customwere subsequently chromatographed a second time on a silica gel S/CH2Cl2 column (φ 2.4 cm, height 88 cm)
  3. customA group of fractions (2.5 g) from the second chromatography crystallized from a hexane/diisopropyl ether 3:1 solution

Sources & evidence

ORD record
ord-076d4729a1704c628dde28d2baba13b6
Source dataset
uspto-grants-1991_03
Patent number
US04999352

Reaction notes

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