2,3-Dihydroxybutanedioic Acid → HCID 534329, compound

HRID 2291598Notes

Reaction equation

HRID 2291598 reaction equation
[C:1]([OH:10])(=[O:9])[CH:2]([CH:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].C(N([CH2:16][CH3:17])CC)C.[CH2:18](Br)[CH:19]=[CH2:20].[CH3:22]N(C=O)C>>[C:1]([O:10][CH2:22][CH:16]=[CH2:17])(=[O:9])[CH:2]([CH:4]([C:6]([O:8][CH2:18][CH:19]=[CH2:20])=[O:7])[OH:5])[OH:3]

Participants

5

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 6228DimethylformamideHCID 7841Allyl bromideHCID 8471Triethylamine

Product 1

HCID 534329HCID 534329, compound

Procedure

Tartaric acid (450 g., 3.0 mols) was slurried in 600 ml. DMF and cooled to 0°-5° C. in an ice bath. Triethylamine (835 ml., 6.0 mols) was added and the resulting solution recooled to 0°-5° C. Allyl bromide (519 ml., 6.0 mols) was then added. An exotherm was noted. The resulting slurry was stirred at room temperature and by-product triethylamine hydrobromide recovered by filtration. The filtrate was diluted with 1.5 l. of ethyl acetate, washed 3×300 ml. H2O, dried over Na2SO4 and stripped to yield title product as an oil, 434 g.; 1H-nmr (CDCl3) delta 3.42 (2H, br.s), 4.5-4.8 (6H, complex), 5.0-5.4 (4H, complex), 5.6-6.2 (2H, complex).

Workup

  1. customrecooled to 0°-5° C
  2. filtrationby-product triethylamine hydrobromide recovered by filtration
  3. additionThe filtrate was diluted with 1.5 l
  4. washof ethyl acetate, washed 3×300 ml
  5. dry with materialH2O, dried over Na2SO4

Sources & evidence

ORD record
ord-dbe9bc563fa040799ea207905c41c2f1
Source dataset
uspto-grants-1989_01
Patent number
US04797394

Reaction notes

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