Imidazole → HCID 21527995, compound

HRID 1658563Notes

Reaction equation

HRID 1658563 reaction equation
[CH:1]#[C:2][CH2:3][CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8].[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1.CN(C)C=O>CCOCC>[C:10]([Si:14]([O:9][CH:4]([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][C:2]#[CH:1])([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1036561-Octyn-4-ol

Product 1

HCID 21527995HCID 21527995, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture consisting of 5 parts of 1-octyn-4(RS)-ol, 6.6 parts of tertiary-butyldimethylsilyl chloride, 6.8 parts of imidazole and 10 parts by volume of dimethylformamide is stirred at room temperature for about 16 hours, then is poured into ether. The resulting organic solution is washed several times with water, then dried over anhydrous sodium sulfate and stripped of solvent under reduced pressure to afford 1-octyn-4(RS)-ol tertiary-butyldimethylsilyl ether, which exhibits a nuclear magnetic resonance maximum at δ0.9.

Workup

  1. washThe resulting organic solution is washed several times with water
  2. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-b2d98091d36646d091cead95e614fd1b
Source dataset
uspto-grants-1976_06
Patent number
US03965143

Reaction notes

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