2,3-Dihydroxybutanedioic Acid → HCID 19002906, compound

HRID 2259517Notes

Reaction equation

HRID 2259517 reaction equation
[OH:1][CH:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#N)[CH:3]=[CH2:4].CC(C[AlH]CC(C)C)C.C(O)(=O)C(C(C(O)=O)O)[OH:24]>C1COCC1>[OH:1][CH:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:24])[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 14487Diisobutylaluminum hydrideHCID 19002915HCID 19002915, compound

Product 1

HCID 19002906HCID 19002906, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the nitrile (Step 1) (17.0 g, 0.107 mmol) in THF (465 mL) at -78° C. was added dropwise a DIBAL solution (157 mL, 0.235 mmol). The resulting mixture was brought slowly to 0° C. After completion, the reaction mixture was poured over 10% aqueous tartaric acid solution (1 L). After stirring for a period of 1 hr., the title product was extracted with EtOAc and purified by flash chromatography (40% to 50% EtOAc in hexane) to afford 15 g (88%) of the aldehyde.

Workup

  1. customwas brought slowly to 0° C
  2. extraction, the title product was extracted with EtOAc
  3. custompurified by flash chromatography (40% to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-dc7dd63b8a6248df8dff372ca858704e
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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