2,4-Pentanediol → N-Acetyl-2-pyrroline

HRID 2308824Notes

Reaction equation

HRID 2308824 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[O:9]C)(=[O:3])[CH3:2].CC(O)CC(O)C.CN1CCCC1=O>O.CCOC(C)=O>[C:1]([N:4]1[CH2:8][CH2:7][CH:6]=[CH:5]1)(=[O:3])[CH3:2].[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[OH:9])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 122622,4-Pentanediol2×HCID 13387N-methyl-2-pyrrolidoneHCID 127112051-(2-Methoxypyrrolidin-1-yl)ethan-1-one2×

Product 2

HCID 10909522N-Acetyl-2-pyrrolineHCID 13113443N-acetyl-2-hydroxypyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Reaction of N-Acetyl-2-methoxypyrrolidine (E) with 2,4-Pentandiol. One g of N-acetyl-2-methoxypyrrolidine (largely E plus lesser an amounts of B, C and D), 0.9 g of 2,4-pentandiol and 240 mg of N-methyl-2-pyrrolidone internal standard were heated at 50°-55° C. in 1 mL of H2O. A separate sample was heated in 1 mL of EtOAc. Results in both samples were similar: rapid initial formation of a small peak at 8.02 min (cyclic hemiamidal of the diol?), followed by growth of major product peaks at 8.35 and 8.73 min, the epimeric cyclic acetals. Small quantities of dehydrated product G (r.t.=4.75 min), and in the aqueous sample, N-acetyl-2-hydroxypyrrolidine, F (before A at ~5.6 min) were also produced. One of the diols appeared to react faster and to a greater extent than the other. Measurements at 3-4 hr were close to the overnight values: ~87% conversion of A, 60-70% of B and essentially quantitative conversion of C and D.

Workup

  1. customResults in both samples
  2. customfollowed by growth of major product peaks at 8.35 and 8.73 min

Sources & evidence

ORD record
ord-e4987d08e2af426abd05a1816f3b8e24
Source dataset
uspto-grants-1987_09
Patent number
US04691026

Reaction notes

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