Water → HCID 68904984, compound

HRID 491404

Reaction equation

HRID 491404 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:13]([O:20][CH2:21][CH2:22][OH:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[K+].O>C1COCC1>[CH2:13]([O:20][CH2:21][CH2:22][O:23][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 121412-(Benzyloxy) ethanolHCID 3847769Ethyl 2-bromoisonicotinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 68904984HCID 68904984, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 2-bromoisonicotinate (575 mg, MATRIX) in THF (25 ml) was added with ethylene glycol monobenzyl ether (710 μl, TCI), cooled to 0° C., and added with potassium t-butoxide (420 mg, TCI), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added with purified water (15 ml), and extracted with ethyl acetate (30 ml×2). The organic layers were combined, washed with saturated brine, and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Flash, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate ii-01).

Workup

  1. extractionextracted with ethyl acetate (30 ml×2)
  2. washwashed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (Flash, hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a07367f730934f9f9f4064504dac7871
Source dataset
uspto-grants-2009_05
Patent number
US07531533B2

Linked notes

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