Ethylene Glycol → HCID 13689820, compound

HRID 1719666Notes

Reaction equation

HRID 1719666 reaction equation
[C:1]([CH:4]1[C:7](=[O:8])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:5]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:3])[CH3:2].[CH2:30](O)[CH2:31][OH:32].O.ClCCl>O1CCOCC1>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[CH2:9][N:6]1[C:7](=[O:8])[CH:4]([C:1]2([CH3:2])[O:32][CH2:31][CH2:30][O:3]2)[C:5]1([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6344DichloromethaneHCID 13422984HCID 13422984, compound

Product 1

HCID 13689820HCID 13689820, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

25.5 g (0.063 moles) of diethyl 3-acetyl-1-(2,4-dimethoxybenzyl)4-oxo-2,2-azetidine-dicarboxylate prepared according to Example 1e), 6.8 ml (0.126 moles, 7.8 g) of ethylene glycol and 15.8 ml (0.126 moles, 17.9 g) of borotrifluoride diethyl etherate in 100 ml of dry dioxane are allowed to stand at room temperature for 3 days, whereupon 150 ml of water and 150 ml of dichloromethane are added to the reaction mixture. Thereafter the organic phase is separated and shaken with 50 ml of a 5% aqueous sodium hydrogencarbonate solution and 50 ml of water. The organic phase is separated again, dried with magnesium sulfate, filtered and the filtrate is evaporated. 23.6 g (84%) of diethyl 1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxo-2,2-azetidine-dicarboxylate are obtained.

Workup

  1. additionare added to the reaction mixture
  2. customThereafter the organic phase is separated
  3. customThe organic phase is separated again
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-eb46ad323647491290cd700a9cffdfa1
Source dataset
uspto-grants-1985_09
Patent number
US04541955

Reaction notes

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