Imidazole → HCID 12786186, compound

HRID 848894Notes

Reaction equation

HRID 848894 reaction equation
[Cl:1][CH2:2][C:3]([OH:11])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6].N1C=CN=C1.[CH3:17][Si:18]([CH3:21])([CH3:20])Cl.C(=O)(O)[O-].[Na+]>CCCCCC.CN(C)C=O>[Cl:1][CH2:2][C:3]([O:11][Si:18]([CH3:21])([CH3:20])[CH3:17])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 12786185HCID 12786185, compound

Product 1

HCID 12786186HCID 12786186, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred, ice-cold solution of 7.22 g. of 4-chloromethyl-4-hydroxy-1-octyne and 7.16 g. of imidazole in 28 ml. of dimethylformamide is added 6.5 ml. of trimethylchlorosilane via a syringe during 15 minutes. The resulting mixture is stirred at room temperature overnight, diluted with hexane and poured into a mixture of ice and saturated sodium bicarbonate solution. The hexane solution is separated, washed with saturated sodium bicarbonate, water and brine, dried over ahydrous sodium sulfate and concentrated in vacuo to give 11.8 g. of a colorless liquid which is vacuum distilled at b.p. 50°-57° C./3.5-4 mm. to give 9.7 g. of product as a colorless liquid; PMR δ 3.58 (s), 2.50 (d), 1.99 (t), 0.87 (s,OTMS).

Workup

  1. customThe hexane solution is separated
  2. washwashed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried over ahydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give 11.8 g
  6. distillationdistilled at b.p. 50°-57° C./3.5-4 mm
  7. customto give 9.7 g

Sources & evidence

ORD record
ord-85399cb1bb3443dfb88fce12e7766fee
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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