Citric Acid → HCID 67577770, compound

HRID 481940Notes

Reaction equation

HRID 481940 reaction equation
[OH:1][C@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2/[CH:12]=[CH:13]/[C:14](OC)=[O:15])[CH2:3]1.[AlH](CC(C)C)CC(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.CCCCCC>[OH:15][CH2:14]/[CH:13]=[CH:12]/[C@@H:11]1[C@:18]2([CH3:26])[C@H:8]([C@H:7]3[C@H:21]([CH2:20][CH2:19]2)[C@:22]2([CH3:25])[C:4]([CH2:3][C@@H:2]([OH:1])[CH2:24][CH2:23]2)=[CH:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14487Diisobutylaluminum hydrideHCID 13301910HCID 13301910, compound

Product 1

HCID 67577770HCID 67577770, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4.85 g of methyl (E)-3β-hydroxypregna-5,20-diene-21-carboxylate (Pouzar, V. et al., Collect. Czech. Chem. Commun, 1990, 55,1243), in 200 ml of anhydrous tetrahydrofurane, 81 ml of i-Bu2AlH (1M) in hexane were added dropwise in a nitrogen atmosphere at -78° C. After two hours the reaction mixture was treated with an aqueous solution of citric acid (30 g in 100 ml of water). The mixture was filtered on Celite and the residue washed with ethyl acetate. The organic solution was dehydrated over anhydrous sodium sulfate and evaporated to dryness under vacuum, to give 4.25 g of (E)-21-hydroxymethylpregna-5,20-dien-3β-ol as a white solid.

Workup

  1. filtrationThe mixture was filtered on Celite
  2. washthe residue washed with ethyl acetate
  3. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-3b6f347286b8405c8715694306e2360c
Source dataset
uspto-grants-1998_08
Patent number
US05792759

Reaction notes

Loading…