HCID 13827091, compound → HCID 504663, compound

HRID 978358Notes

Reaction equation

HRID 978358 reaction equation
[CH3:1][Li].[CH2:3]([O:5][C:6]1[O:11][C:10](=[O:12])[C:9]2[C:13]([CH2:17]Br)=[CH:14][CH:15]=[CH:16][C:8]=2[N:7]=1)[CH3:4]>CCOCC.O1CCCC1>[CH2:3]([O:5][C:6]1[O:11][C:10](=[O:12])[C:9]2[C:13]([CH2:17][CH3:1])=[CH:14][CH:15]=[CH:16][C:8]=2[N:7]=1)[CH3:4]

Participants

5

Reactant 2

HCID 13827091HCID 13827091, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 504663HCID 504663, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

Methyl lithium (4.69 ml, 1.4M, Aldrich) was added to a suspension of cuprous iodide (0.62 gm) in anhydrous ether under argon at -78° C. The solution was stirred at -25° C. for 25 min. This solution was added to a solution of 2-ethoxy-5-bromomethyl-4H-3,1-benzoxazin-4-one (200 mg) in 15 ml anhydrous ether and 3 ml dry tetrahydrofuran at -60° C. Reaction was monitored by TLC until reaction completion. The reaction was quenched with saturated ammonium chloride solution and filtered. The filtrate was extracted in the usual manner. The ethereal layer was washed with water, dried over magnesium sulphate and evaporated to give an oil. The material was purified by thick layer chromatography (Rf =0.75, 3-% ethyl acetate: petroleum ether), to give 2-ethoxy-5-ethyl-4H-3,1-benzoxazin-4-one, m.p. 89°-91° C., H NMR: 1.3, 1.5 (2t, 6H, 2CH3), 3.2 (q, 2H, CH2), 4.5 (q, 2H, OCH2CH3), 7.2 (m, 2H, ArH), 7.6 (t, 1H, ArH).

Workup

  1. customReaction
  2. customwas monitored by TLC until reaction completion
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. filtrationfiltered
  5. extractionThe filtrate was extracted in the usual manner
  6. washThe ethereal layer was washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customto give an oil
  10. customThe material was purified by thick layer chromatography (Rf =0.75, 3-% ethyl acetate: petroleum ether)

Sources & evidence

ORD record
ord-229cdcf9dcae47bb907b54dde74fdee0
Source dataset
uspto-grants-1987_05
Patent number
US04665070

Reaction notes

Loading…