Ethyl orthoformate → HCID 54151626, compound

HRID 1953929Notes

Reaction equation

HRID 1953929 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].C(OC(OCC)OCC)C.[C:37]([C@@H:42]([C@H:44]([C:46]([O:48][CH2:49][CH3:50])=[O:47])O)[OH:43])([O:39][CH2:40][CH3:41])=[O:38].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:49]([O:48][C:46]([C@H:44]1[C@H:42]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[O:43][CH:25]([C:22]2[CH:23]=[CH:24][C:19]([C:16]3[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:18][CH:17]=3)=[CH:20][CH:21]=2)[O:26]1)=[O:47])[CH3:50]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 6993580Diethyl tartrateHCID 23295483HCID 23295483, compound

Product 1

HCID 54151626HCID 54151626, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.706 g of 4'-(6-acryloxyhexyloxy)biphenyl-4-carboxaldehyde, 1 ml of orthoformic acid triethyl ester, 0.7 ml of diethyl L-tartrate, 27 mg of BHT, 6.8 mg of 4-toluenesulphonic acid monohydrate and 10 ml of toluene was allowed to stand for 1 hour at room temperature, then heated for 2.5 hours to boiling, the solvent being distilled off and replaced by fresh toluene. After the addition of 3 drops of triethylamine and cooling, it was diluted with diethyl ether, washed with water, dried over sodium sulphate, filtered and concentrated at 40° C. in vacuo. The oily residue was chromatographed on 45 g of silica gel with hexane/ethyl acetate 4:1. Recrystallisation from ethyl acetate resulted in 0.18 g (4R,5R)-2-[4-(6-acryloxyhexyloxy)biphenyl-4-yl]-1,3-dioxolane-4,5-dicarboxy acid diethyl ester; boiling point (C-I) 65° C.

Workup

  1. temperatureheated for 2.5 hours
  2. distillationthe solvent being distilled off
  3. additionAfter the addition of 3 drops of triethylamine
  4. temperaturecooling
  5. additionit was diluted with diethyl ether
  6. washwashed with water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated at 40° C. in vacuo
  10. customThe oily residue was chromatographed on 45 g of silica gel with hexane/ethyl acetate 4:1
  11. customRecrystallisation from ethyl acetate
  12. customresulted in 0.18 g (4R,5R)-2-[4-(6-acryloxyhexyloxy)biphenyl-4-yl]-1,3-dioxolane-4,5-dicarboxy acid diethyl ester
  13. custompoint (C-I) 65° C.

Sources & evidence

ORD record
ord-e8f419a83c2247a2bb016e6cee4dc008
Source dataset
uspto-grants-2000_09
Patent number
US06120859

Reaction notes

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