Imidazole → HCID 11741865, compound

HRID 375243Notes

Reaction equation

HRID 375243 reaction equation
[CH2:1]([O:15][CH2:16][CH:17]([CH2:19][OH:20])[OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>CN(C=O)C>[CH2:1]([O:15][CH2:16][CH:17]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 646743-(Tetradecyloxy)-1,2-propanediol

Product 1

HCID 11741865HCID 11741865, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of rac-1-O-tetradecylglycerol (57.7 g, 0.2 mol), tert-butyldimethylsilyl chloride (33.2 g, 0.22 mol), imidazole (30.0 g, 0.44 mol), and DMF (300 ml) was stirred at room temperature for 1 day. The solvent was evaporated to dryness in vacuo at 70° C. and the residue was partioned between H2O and diethyl ether (500 ml each). The organic layer was dried over Na2SO4 and then evaporated to dryness. The oily residue was further evaporated by using a high vacuum at 70° C. The crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield).

Workup

  1. customThe solvent was evaporated to dryness in vacuo at 70° C.
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated to dryness
  4. customThe oily residue was further evaporated
  5. customat 70° C
  6. customThe crude product, essentially homogeneous by TLC, was used for the next step without further purification (100% yield)

Sources & evidence

ORD record
ord-44c230f2b6b1470eb7c361a66407ae30
Source dataset
uspto-grants-1996_01
Patent number
US05484911

Reaction notes

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