Diethyl Ether → HCID 20337455, compound

HRID 1706270Notes

Reaction equation

HRID 1706270 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[O:22][CH3:23])(O)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[O:22][CH3:23])[CH3:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 20337453HCID 20337453, compound

Product 1

HCID 20337455HCID 20337455, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a 0° C. solution of 2-(2,5-dimethoxyphenyl)-2-hydroxypropyl 2-phenylethyl ether (550 mg., 1.74 mM) in pyridine (2 ml.) is added dropwise phosphorous oxychloride (477 ml., 5.22 mM). The reaction is allowed to warm to 20° C. over a 1.5 hour period. It is then stirred for 1.5 hours at 20° C. and then added to ether (150 ml.) and 15% sodium carbonate (100 ml.). The organic phase is separated and washed with 15% sodium carbonate (3×50 ml.), dried over magnesium sulfate and evaporated to an oil. The oil is dissolved in absolute ethanol (15 ml.), 10% palladium-on-carbon (100 mg.) added and the mixture stirred under one atmosphere of hydrogen gas. When hydrogen uptake ceases, the reaction is filtered through diatomaceous earth and the filtrate evaporated to an oil. The oil is purified via preparative layer chromatography on silica gel plates, eluting with 6:1 pentane: ether to yield 2-(2,5-dimethoxyphenyl)propyl 2-phenylethyl ether.

Workup

  1. customThe organic phase is separated
  2. washwashed with 15% sodium carbonate (3×50 ml.)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to an oil
  5. dissolutionThe oil is dissolved in absolute ethanol (15 ml.)
  6. addition10% palladium-on-carbon (100 mg.) added
  7. stirringthe mixture stirred under one atmosphere of hydrogen gas
  8. filtrationWhen hydrogen uptake ceases, the reaction is filtered through diatomaceous earth
  9. customthe filtrate evaporated to an oil
  10. customThe oil is purified via preparative layer chromatography on silica gel plates
  11. washeluting with 6:1 pentane

Sources & evidence

ORD record
ord-a88fbd950a4f46f4a2bdced2472b21de
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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