Ethyl orthoformate → HCID 70147355, compound

HRID 581368Notes

Reaction equation

HRID 581368 reaction equation
[CH3:1][CH:2]([CH2:4][C@H:5](NC(CNC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](N)CC1C=CC(O)=CC=1)=O)CC(N)=O)=O)CC1C2C(=CC=CC=2)NC=1)=O)CC(N)=O)=O)CO)=O)CC1C=CC=CC=1)=O)=O)C(N[C@H](C(N[C@H](C(N)=O)CC1C=CC=CC=1)=O)CCCN=C(N)N)=O)[CH3:3].[CH:95]([O:102][CH2:103][CH3:104])([O:99]CC)OCC.CC(C)=CC=O>C(O)CO>[CH3:1][C:2]([CH3:3])=[CH:4][CH3:5].[O:102]1[CH2:103][CH2:104][O:99][CH2:95]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 610203-Methyl-2-butenalHCID 25240297374675-21-5

Product 1

HCID 70147355HCID 70147355, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
4 °C

Procedure

0.5 undried catalyst KP-10 (Sud-Chemie), 79.6 g triethyl orthoformate and 48.2 g 3-methyl-crotonaldehyde were placed in a flask in a nitrogen atmosphere in 34.3 g ethyleneglycol and stirred at 4° C. for 1.5 hours. Then the catalyst was filtered off through a suction filter and washed with 20 ml ethanol. The product was concentrated and isolated by fractionated distillation (2 fractions at 204 mbar/107° C). The 3-methyl-2-butene-1,3-dioxolane fractions obtained had a content of 81% (39.2 g) and 86.9% (3 g) (47% yield).

Workup

  1. filtrationThen the catalyst was filtered off through a suction
  2. filtrationfilter
  3. washwashed with 20 ml ethanol
  4. concentrationThe product was concentrated
  5. customisolated by fractionated distillation (2 fractions at 204 mbar/107° C)

Sources & evidence

ORD record
ord-40e1088005544d54b070a4b2bb9c1ad7
Source dataset
uspto-grants-1999_07
Patent number
US05919953

Reaction notes

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