Diisopropyl diazene-1,2-dicarboxylate → HCID 67538659, compound

HRID 570861Notes

Reaction equation

HRID 570861 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]([O:38][CH2:39][CH:40]([CH2:45][CH3:46])[CH2:41][CH2:42][CH2:43][CH3:44])=[O:37])=[CH:30][CH:29]=1>CN(C)C=O>[OH:6][C:5]1[C@@H:7]([C@H:9]([OH:10])[CH2:11][O:12][C:28]2[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]([O:38][CH2:39][CH:40]([CH2:45][CH3:46])[CH2:41][CH2:42][CH2:43][CH3:44])=[O:37])=[CH:30][CH:29]=2)[O:8][C:2](=[O:1])[C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22105034HCID 22105034, compoundHCID 54670067L-Ascorbic Acid

Product 1

HCID 67538659HCID 67538659, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

20 g of ascorbic acid (113.5 mmol; 1 eq.) are dissolved in 100 ml of di-methylformamide in an argon-flushed 3-necked flask, 32.76 g of triphenyl-phosphine are added, and 25.3 g of diisopropyl azodicarboxylate (124.9 mmol; 1.1 eq) are slowly added dropwise at 0° C. After 30 min, the 2-ethylhexyl(E)-3-(4-hydroxyphenyl)acrylate (32.95 g; 1.05 eq; 119.2 mmol) dissolved in 45 ml of dimethylformamide is added dropwise. After 30 min at 0° C., the mixture is stirred at room temperature for a further 6 hrs. The reaction solution is evaporated to dryness, suspended in 100 ml of ethyl acetate/hexane 1:2, filtered, and the product is precipitated as a white solid by addition of 100 ml of hexane.

Workup

  1. customflushed 3-necked flask
  2. addition32.76 g of triphenyl-phosphine are added
  3. additionis added dropwise
  4. waitAfter 30 min at 0° C.
  5. customThe reaction solution is evaporated to dryness
  6. filtrationfiltered
  7. customthe product is precipitated as a white solid by addition of 100 ml of hexane

Sources & evidence

ORD record
ord-6beb1256f8dd46ae9f657da14ad9a253
Source dataset
uspto-grants-2015_05
Patent number
US09023889B2

Reaction notes

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