Ethyl orthoformate → HCID 69493699, compound

HRID 916995Notes

Reaction equation

HRID 916995 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH:5]([OH:13])[CH:6]([OH:12])[CH2:7][C:8]([O:10][CH3:11])=[O:9].[CH:15](OCC)(OCC)[O:16][CH2:17][CH3:18]>C1(C)C=CC=CC=1>[CH3:11][O:10][C:8](=[O:9])[CH2:7][CH:6]1[CH:5]([CH2:4][C:3]([O:2][CH3:1])=[O:14])[O:13][CH:15]([O:16][CH2:17][CH3:18])[O:12]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 228898HCID 228898, compound

Product 1

HCID 69493699HCID 69493699, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,4-dihydroxy-hexanedioic acid dimethyl ester (Ex-14A, 8.8 g, 43 mmol) in toluene (65 mL) was added triethyl orthoformate (12.6 g, 85.4 mmol) and the mixture was heated at reflux with a Dean-Stark trap for 24 h. The reaction mixture was then distilled to remove toluene and excess triethyl orthoformate and dried in vacuo to give (2-ethoxy-5-methoxycarbonylmethyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester as a colorless oil (11.0 g, 99%). This material used without further purification. 1H-NMR (300 MHz, CDCl3) δ5.80 (s, 1H),4.41 (q, 1H, J=6.3 Hz), 4.28 (q, 1H, J=6.3 Hz), 3.71 (s, 6H), 3.78 (q, 2H, J=7.2 Hz), 2.83 (dd, 1H, J=9.3, 6.7 Hz), 2.70 (dd, 1H, J=6.7, 3.0 Hz), 1.22 (t, 3H, J=7.2 Hz). HRMS (EI) calcd for C11H18O7 (M−H), 261.0974; found, 261.0970.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux with a Dean-Stark trap for 24 h
  3. distillationThe reaction mixture was then distilled
  4. customto remove toluene and excess triethyl orthoformate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e29255e8840545b2b89a757e9a66314f
Source dataset
uspto-grants-2007_09
Patent number
US07271274B2

Reaction notes

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