Ethylene Glycol → HCID 11448548, compound

HRID 250510Notes

Reaction equation

HRID 250510 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][C:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[CH2:16]([OH:19])[CH2:17]O.[C:20]1(C)C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:20])=[O:13])[O:19][CH2:16][CH2:17][O:15]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 25272440HCID 25272440, compound

Product 1

HCID 11448548HCID 11448548, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

To a solution of 5-(4-fluorophenyl)-5-oxopentanoate (2.26 g, 10 mmol) in toluene (60 ml) was added ethylene glycol (1.95 ml, 35 mmol) and p-toluenesulfonic acid monohydrate (60 mg, 0.32 mmol) and the mixture refluxed in a Dean-Stark apparatus under nitrogen for 17 h. The toluene was removed by rotary evaporator and the residue treated with sodium bicarbonate solution (5%, 50 ml) and extracted with ether (2×50 ml). The ether extract was washed with brine (1×50 ml), dried (Na2SO4) and evaporated to give methyl 4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]butanoate (9) as a pale yellow oil (2.47 g, 91%). 1H nmr (CDCl3, 300 MHz) 1.6-1.7, m, H3; 1.9, m, H4; 2.30, t (7.5 Hz), H2; 3.64, s, OMe; 3.7-3.8, m, CH2O; 3.95-4.05, m, CH2O; 7.01, m, H3′,5′; 7.41, m, H2′,6′. ESI (+ve) MS m/z 269 (M+H, 45%).

Workup

  1. temperaturethe mixture refluxed in a Dean-Stark apparatus under nitrogen for 17 h
  2. customThe toluene was removed by rotary evaporator
  3. additionthe residue treated with sodium bicarbonate solution (5%, 50 ml)
  4. extractionextracted with ether (2×50 ml)
  5. extractionThe ether extract
  6. washwas washed with brine (1×50 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-42933957637f4592bbf2ffe0fb03b58f
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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