Acetoacetic Acid → HCID 131716691, compound

HRID 1073465Notes

Reaction equation

HRID 1073465 reaction equation
[C:1]1([CH2:7][O:8][C@H:9]2[C@H:18]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:17]([CH2:27][OH:28])[O:16][C@@:10]2([OH:15])[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(CC(O)=O)=O.C(O)(=O)C>C[O-].[Na+].CO>[C:1]1([CH2:7][O:8][C@H:9]2[C@H:18]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:17]([CH2:27][OH:28])[O:16][C:10]2([OH:15])[C:11]([O:13][CH3:14])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 96Acetoacetic AcidHCID 176Acetic AcidHCID 131716692HCID 131716692, compound

Product 1

HCID 131716691HCID 131716691, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A solution of 4.25 g of 3,4-bis-O-(phenylmethyl)-alpha-D-arabino-hexulofuranosonic acid, methyl ester, diacetate in 45 ml of 1.0M sodium methoxide in methanol was stirred at 25° for 20 minutes, treated with 4.1 ml of acetic acid, and concentrated. The residue was partitioned with ethyl acetate and water. The organic layer was washed with water and brine, dried, and concentrated. The residue was subjected to chromatography on silica gel to give an oil, CMR δ 53.3 (CH3OCO).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned with ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil, CMR δ 53.3 (CH3OCO)

Sources & evidence

ORD record
ord-3b0bfc832dd344d895d8a09f1818d345
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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