N-(2-Hydroxyethyl)imidazole → HCID 69024950, compound

HRID 1865769Notes

Reaction equation

HRID 1865769 reaction equation
[CH2:1]([O:28][CH2:29]Cl)[CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[N:31]1([CH2:36][CH2:37][OH:38])[CH:35]=[CH:34][N:33]=[CH:32]1.C(O[K])(C)(C)C>O1CCCC1>[CH2:1]([O:28][CH2:29][O:38][CH2:37][CH2:36][N:31]1[CH:35]=[CH:34][N:33]=[CH:32]1)[CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3]

Participants

5

Reactant 3

HCID 74168N-(2-Hydroxyethyl)imidazoleHCID 86619920HCID 86619920, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 69024950HCID 69024950, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, 43.7 g of chloromethyl cholestanyl ether (24) was added to a mixture of 11.2 g of 2-(1H-imidazol-1-yl)ethanol (23), 11.2 g of t-butoxypotassium, and 100 g of tetrahydrofuran. Then the mixture was stirred at room temperature for 10 hours. Subsequent standard aqueous work-up and purification by silica gel column chromatography gave 38.5 g of 1-[2-(cholestanyloxymethoxy)ethyl]imidazole (Quencher 5). Yield 75%.

Workup

  1. customSubsequent standard aqueous work-up and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-9c611edeb93d4d1984bd0c93ad24224c
Source dataset
uspto-grants-2009_12
Patent number
US07629108B2

Reaction notes

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