Diethyl Ether → HCID 54028132, compound

HRID 2286790Notes

Reaction equation

HRID 2286790 reaction equation
CCO[CH2:4][CH3:5].CN(C)P(=O)(N(C)C)N(C)C.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].O([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Br)C1C=CC=CC=1>O.CCCCCC>[CH:32]([CH:31]([CH:30]=[C:37]([C:5]1[CH:4]=[CH:36][CH:37]=[CH:30][CH:31]=1)[CH3:36])[C:17]([OH:18])=[O:20])([CH3:33])[CH3:35]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 945441-(Bromomethyl)-3-phenoxybenzene

Product 1

HCID 54028132HCID 54028132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To 2.14 g (10 mmole) of the thus-obtained acid, 10 ml ether and 10 ml hexamethylphosphorictriamide (HMPT), under nitrogen, is added 1.45 g (10.5 mmole) potassium carbonate and 2.76 g (10.5 mmole) m-phenoxybenzyl bromide. The reaction is stirred about 16 hr and then poured into hexane and water. The organic phase is washed with water, saturated sodium chloride, and dried over calcium sulfate. Solvent is removed by rotoevaporation to yield the m-phenoxybenzyl ester of 2-isopropyl-4-phenyl-3-pentenoic acid, which can be further purified by preparatory thin layer chromatography (prep. TLC) eluting with 2.5% ethyl acetate/hexane, MS m/e 400 (M+, 15), 183 (100).

Workup

  1. washThe organic phase is washed with water, saturated sodium chloride
  2. dry with materialdried over calcium sulfate
  3. customSolvent is removed by rotoevaporation

Sources & evidence

ORD record
ord-4e7f5d35b2b441c98db25bebabab2025
Source dataset
uspto-grants-1981_05
Patent number
US04267359

Reaction notes

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