Water → HCID 70022904, compound

HRID 989612Notes

Reaction equation

HRID 989612 reaction equation
[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][CH2:21][C@H:20]4[C:11](=[CH:12][CH2:13][C:14]5[CH2:15][C:16]([O:23]C)=[CH:17][CH2:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1.O.O.O.C(O)(=O)C(O)=O>ClCCl.C1COCC1.CO>[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][CH2:21][C@H:20]4[C:11](=[CH:12][CH2:13][C:14]5[CH2:15][C:16](=[O:23])[CH2:17][CH2:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1

Participants

7

Reactant 3

HCID 962WaterHCID 61373Oxalic acid dihydrateHCID 70021403HCID 70021403, compound

Product 1

HCID 70022904HCID 70022904, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the enol ether 2 (0.5 g, 1.52 mmol) in dichloromethane (30 mL), THF (20 mL) and methanol (20 mL) was added water (30 mL) followed by oxalic acid dihydrate (1.2 g, 9.5 mmol) and the resulting biphasic mixture was vigorously stirred for 8.5 h. The layers were separated and the aqueous layer washed with dichloromethane (2×20 mL). The organic layers were combined, dried over anhydrous potassium carbonate and concentrated to give the ketone 3 as a glassy solid (0.47 g, 98%).

Workup

  1. customThe layers were separated
  2. washthe aqueous layer washed with dichloromethane (2×20 mL)
  3. dry with materialdried over anhydrous potassium carbonate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9b2ea93336c04fbb9be4f692f1cd80cc
Source dataset
uspto-grants-2002_10
Patent number
US06458778B1

Reaction notes

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