2,3-Dihydroxybutanedioic Acid → HCID 22857730, compound

HRID 2259510Notes

Reaction equation

HRID 2259510 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH:20]=1)[O:11][CH2:12][C:13](=[CH2:18])[C:14](OC)=[O:15].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(O)(=O)C(C(C(O)=O)O)O.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@H:10]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH:20]=1)[O:11][CH2:12][C:13](=[CH2:18])[CH2:14][OH:15]

Participants

7

Reactant 5

HCID 8752,3-Dihydroxybutanedioic AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 22857742HCID 22857742, compound

Product 1

HCID 22857730HCID 22857730, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the ester of Step 3 (29.69 g, 59 mmol) in 300 mL of CH2Cl2 at -78° C. was added slowly a solution of diisobutylaluminum hydride 1.5M in toluene (99 mL, 149 mmol) and the mixture was stirred at -78° C. for 30 min. 2M Tartaric acid was then added and the solution was neutralized with 10 N NaOH. The product was extracted in EtOAc, dried over Na2SO4, and concentrated to give 26.90 g, 96%, of the title alcohol.

Workup

  1. extractionThe product was extracted in EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give 26.90 g, 96%

Sources & evidence

ORD record
ord-1611a937fdb3467eaf3d03dec01bb17e
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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