Phosphorus oxide (P4O10) → HCID 18635748, compound

HRID 1638557Notes

Reaction equation

HRID 1638557 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][C@@H:11]3[O:13][C:14]4[C:20]([C:21]([NH2:23])=O)=[CH:19][CH:18]=[CH:17][C:15]=4[O:16][C@H:10]3[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[C:1]1([CH2:7][N:8]2[CH2:12][C@@H:11]3[O:13][C:14]4[C:20]([C:21]#[N:23])=[CH:19][CH:18]=[CH:17][C:15]=4[O:16][C@H:10]3[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 18635749HCID 18635749, compound

Product 1

HCID 18635748HCID 18635748, compoundYield 68.5%

Procedure

An intimate mixture of Compound E (1.24 g) and phosphorus pentoxide (0.6 g) was heated to 165°. Two further aliquots of phosporus pentoxide (0.6 g each) were added at 10 minute intervals, mixing well in, while maintaining the temperature in the range 165° to 180°. Ten minutes after the final addition the solid mass was triturated with aqueous potassium hydroxide, ethyl acetate mixture and stirred well until free of solid. Evaporation of the organic layer gave a brown oil which was chromatographed on silica gel (50 g). Elution with ethyl acetate:petrol b.pt. 60°-80° (1:1) gave an oil (0.8 g) which solidified on trituration, with petrol, b.pt. 60°-80°. The product was collected, washed with petrol and dried to give the title compound as a buff coloured solid (0.57 g) m.pt. 101°-103°, NMR τ (CDCl3) 2.74 (5H, s, Ph), 2.5-3.4 (3H, m, aromatic), 5.4-6.1 (2H, m, 3a-H, 9a-H), 6.18 (2H, s, CH2Ph), 6.5-7.4 (4H, m, 1-H2, 3-H2).

Workup

  1. temperaturewas heated to 165°
  2. additionTwo further aliquots of phosporus pentoxide (0.6 g each) were added at 10 minute intervals
  3. additionmixing well in,
  4. temperaturewhile maintaining the temperature in the range 165° to 180°
  5. additionTen minutes after the final addition the solid mass
  6. customwas triturated with aqueous potassium hydroxide, ethyl acetate mixture
  7. customEvaporation of the organic layer
  8. customgave a brown oil which
  9. customwas chromatographed on silica gel (50 g)
  10. washElution with ethyl acetate

Sources & evidence

ORD record
ord-81ca75ba8bff48a0aa1d2fde68a51cb6
Source dataset
uspto-grants-1989_11
Patent number
US04880801

Reaction notes

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