Water → HCID 54224567, compound

HRID 2294761Notes

Reaction equation

HRID 2294761 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH:18]([CH3:20])[CH3:19])CC)(C)C.[I-].Cl[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N+]=1C.[OH2:30]>ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:1](=[O:8])[CH2:2][O:30][CH2:25][CH2:26][CH2:27][CH2:28][CH2:23][CH2:25][CH2:26][CH2:27][CH2:28][CH2:23][CH2:3][CH2:4][CH2:5][CH2:20][CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 121412-(Benzyloxy) ethanolHCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 54224567HCID 54224567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the carboxyl acid derivative prepared in Reference Example 4 (698 mg) and 2-(benzyloxy)ethanol (710 mg) in dichloromethane (10 ml) was added diisopropylethylamine (2.2 ml), and 2-chloro-1-methylpyridinium iodide (891 mg), successively, and the reaction solution was stirred for 1.5 hours. Water was added to the reaction solution and the solution was extracted with dichloromethane (twice). The organic layer was washed with dilute hydrochloric acid and a saturated aqueous solution of sodium chloride, successively, dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate 10:1) to give the title compound (425 mg) having the following physical data. TLC: Rf 0.63 (n-hexane:ethyl acetate=3:1),

Workup

  1. extractionthe solution was extracted with dichloromethane (twice)
  2. washThe organic layer was washed with dilute hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate 10:1)

Sources & evidence

ORD record
ord-a2655bbad3f74f5a8ff97c91fedaa43b
Source dataset
uspto-grants-1997_11
Patent number
US05690957

Reaction notes

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