Imidazole → HCID 12786186, compound

HRID 903383Notes

Reaction equation

HRID 903383 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 anhydrous 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 anhydrous 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-81cc847755b74c109de7e3cd337eeecc
Source dataset
uspto-grants-1980_10
Patent number
US04227011

Reaction notes

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