Ethanol → 6-[2-Imidazol-1-yl-1-(4-methoxy-benzyloxymethyl)-ethoxy]-hexanoic acid ethyl ester

HRID 845467Notes

Reaction equation

HRID 845467 reaction equation
[N:1]1([CH2:6][CH:7]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:28](N(CC)CC)[CH3:29].ClC(OCC)=O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N:1]1([CH2:6][CH:7]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:28][CH3:29])=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 702EthanolHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 135902686-[2-Imidazol-1-yl-1-(4-methoxy-benzyloxymethyl)-ethoxy]-hexanoic acid

Product 1

HCID 139048066-[2-Imidazol-1-yl-1-(4-methoxy-benzyloxymethyl)-ethoxy]-hexanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoic acid (Example 1c) (10 g, 0.026 mol) and triethylamine (3.0 g, 0.03 mol.) in dichloromethane (100 ml, dried over 4 A molecular sieves) at -50° C. was treated dropwise with ethyl chloroformate (3.2 g, 0.029 mol.). The solution was allowed to warm up to 0° C. over 0.5 hours, cooled back to -50° C. and treated with ethanol (6 ml, 0.1 mol). The solution was allowed to warm up and then stirred for 15 hours at 18° C. The mixture was then shaken with an aqueous solution of saturated sodium carbonate (500 ml). The organic layer was separated, dried (Na2SO4) and the solvent was evaporated off under reduced pressure to give the crude product which was purified by column chromatography (silica gel, 5% ethanol in chloroform) to give ethyl 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoate as a pale-yellow oil.

Workup

  1. temperaturecooled back to -50° C.
  2. temperatureto warm up
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated off under reduced pressure
  6. customto give the crude product which
  7. customwas purified by column chromatography (silica gel, 5% ethanol in chloroform)

Sources & evidence

ORD record
ord-b8cb347520bf4e68adcbc177f5d510c3
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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