1-Hexyne → HCID 13748694, compound

HRID 2350824Notes

Reaction equation

HRID 2350824 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C([Li])CCC.[CH3:12][C:13]([CH3:24])([C:15](=[O:23])[CH:16]([N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)[CH3:17])[CH3:14]>C1COCC1>[CH3:24][C:13]([CH3:12])([C:15]([CH:16]([N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)[CH3:17])([OH:23])[C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH3:14]

Participants

5

Reactant 3

HCID 127321-HexyneHCID 19846696HCID 19846696, compoundHCID 178418339Butyllithium

Product 1

HCID 13748694HCID 13748694, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of hex-1-yne (0.61 g, 7.5 mmol) in dry THF (30 ml) was added n-butyl lithium (3 ml of 2.6M, 7.5 mmol) at -78° C. under a nitrogen atmosphere. After 15 minutes, a solution of 2,2-dimethyl-4-(1H-imidazol-1-yl)-pentan-3-one (1.26 g, 7 mmol) in dry THF (30 ml) was added dropwise. Upon complete addition the mixture was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was then poured onto ice and extracted with ether (2×250 ml). The ethereal solution was washed with saturated brine solution then dried over anhydrous magnesium sulphate and the solvent removed. The resulting yellow oil was chromatographed (silica gel, petrol/diethyl ether elution) to give the product as a white solid (1.39 g, 76%), mp. 57-59% (Found C, 72.2; H, 10.1; N, 10.8. C16H26N2O requires C 73.3; H, 9.9; N, 10.7%); IR 2950, 1460, 1360, 1270, 1220, 1080 980, 920, 810, 730, 660 cm-1.

Workup

  1. additionUpon complete addition the mixture
  2. additionThe reaction mixture was then poured onto ice
  3. extractionextracted with ether (2×250 ml)
  4. washThe ethereal solution was washed with saturated brine solution
  5. dry with materialthen dried over anhydrous magnesium sulphate
  6. customthe solvent removed
  7. customThe resulting yellow oil was chromatographed
  8. wash(silica gel, petrol/diethyl ether elution)

Sources & evidence

ORD record
ord-8832fa24e32140339288ff0d12933a10
Source dataset
uspto-grants-1989_10
Patent number
US04871389

Reaction notes

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