Acetic Anhydride → HCID 20373156, compound

HRID 1834418Notes

Reaction equation

HRID 1834418 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8].C(OC(=O)C)(=O)C.[PH2](O)=O.[CH:21](=O)[C:22]([CH3:25])([CH3:24])[CH3:23]>I.O>[CH3:1][C:2]1[NH:3][C:4]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 12417PivalaldehydeHCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methylHCID 4124402Phosphinic Acid

Product 1

HCID 20373156HCID 20373156, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24841Hydrogen iodideSolvent

Conditions

Temperature
35 °C

Procedure

2,4-Dimethyl-3 -acetyl-pyrrole (548 mg) was warmed to solution in a mixture of 10 ml of aqueous hydriodic acid, 10 ml of acetic anhydride and 2 ml of hypophosphorous acid. The solution was cooled to 35° C. and 0.85 ml of pivalaldehyde were added. The solution was stirred for ten minutes, by which time the initially dark brown color had changed to yellow, then poured into 125 ml of water. The product separated as a colourless powder (769 mg, 93%), m.p. 156°-163 ° C. For analysis, it was recrystallized from ether-pentane, sublimed at 115° C. (10-4 mm), and again recrystallized by extraction into hexane (thimble) as long colourless plates, m.p. 166°-167° C. after changing to prisms below 130° C. Anal. Calc. for C13H21NO: C, 75.31; H, 10.21; N, 6.76. Found: C, 75.13; H, 10.30; N, 6.58.

Workup

  1. customThe product separated as a colourless powder (769 mg, 93%), m.p. 156°-163 ° C
  2. customFor analysis, it was recrystallized from ether-pentane
  3. customsublimed at 115° C.
  4. customagain recrystallized by extraction into hexane (thimble) as long colourless plates, m.p. 166°-167° C.
  5. customafter changing to prisms below 130° C

Sources & evidence

ORD record
ord-928401dcdcaf4d1eabf987ce015a2783
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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