Acetyl chloride → HCID 70051991, compound

HRID 1729494Notes

Reaction equation

HRID 1729494 reaction equation
C([Cl:4])(=O)C.O[N:6]=[C:7]([C:13](=[O:17])[CH:14]1[CH2:16][CH2:15]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)C.[Pt]>[ClH:4].[NH2:6][CH:7]([C:13](=[O:17])[CH:14]1[CH2:16][CH2:15]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 178472888HCID 178472888, compound

Product 1

HCID 70051991HCID 70051991, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent2×

Procedure

Acetyl chloride (15.35 ml, 16.88 g) was added to a cooled solution of ethyl α-(hydroxyimino)-β-oxocyclopropanepropanoate (20 g) in absolute ethanol (250 ml) before being added to a suspension of 5% platinum on carbon (1.85 g) in absolute ethanol (150 ml). The stirred mixture was then hydrogenated at room temperature and pressure for 5 h. The catalyst was filtered off through a pad of hyflo and the filtrate concentrated in vacuo to give, after azeotroping with toluene (2×80 ml), an off-white solid. This was triturated with ether (500 ml) to give the title compound (14.5 g) as a white solid. m.p. 196°-197° C.

Workup

  1. customwas then hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off through a pad of hyflo
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give
  5. customafter azeotroping with toluene (2×80 ml)
  6. customThis was triturated with ether (500 ml)

Sources & evidence

ORD record
ord-195a4c7f6da0431c8b796e97ed366fc9
Source dataset
uspto-grants-1994_07
Patent number
US05332831

Reaction notes

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