1-Heptyne → 2,2-Dimethyl-3-hydroxy-3-(hept-1-yne-1-yl)-4-(1,2,4-triazol-1-yl)-butane

HRID 358928

Reaction equation

HRID 358928 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C([Li])CCC.[CH3:13][C:14]([CH3:24])([C:16](=[O:23])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1)[CH3:15]>O1CCCC1.CCCCCC>[CH3:15][C:14]([CH3:24])([C:16]([OH:23])([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1)[CH3:13]

Participants

6

Reactant 3

HCID 123501-HeptyneHCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanoneHCID 178418339Butyllithium

Product 1

HCID 137871182,2-Dimethyl-3-hydroxy-3-(hept-1-yne-1-yl)-4-(1,2,4-triazol-1-yl)-butaneYield 26.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of hept-1-yne (3.9 g, 0.041 mol) in dry tetrahydrofuran (30 mls) at -70° C. under nitrogen was added n-butyl lithium (30 mls of a 1.55M solution in hexane) and the resulting mixture stirred for 1 hour. To this mixture was added a solution of 2,2-dimethyl-4-(1,2,-4-triazol-1-yl)-butane-3-one (6.8 g, 0.041 mol) in dry tetrahydrofuran (50 mls), and the resulting mixture was allowed to warm to room temperature. The reaction mixture was partitioned between ethyl acetate and aqueous HCl (1.0M). The aqueous was further extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water, saturated sodium bicarbonate solution and brine, dried (anhydrous MgSO4) and then concentrated in-vacuo to give a yellow oil. Chromatography on silica using gradient elution (diethyl ether 20-80% in petrol) gave the title compound (2.87 g) as a yellow crystalline solid melting point 76°-78° C.).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and aqueous HCl (1.0M)
  2. extractionThe aqueous was further extracted with ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried (anhydrous MgSO4)
  5. concentrationconcentrated in-vacuo
  6. customto give a yellow oil
  7. washChromatography on silica using gradient elution (diethyl ether 20-80% in petrol)

Sources & evidence

ORD record
ord-d78227a473404ac68d82d34c7b00e2fa
Source dataset
uspto-grants-1991_03
Patent number
US04999043

Linked notes

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