Allyl bromide → HCID 178456565, compound

HRID 1609008Notes

Reaction equation

HRID 1609008 reaction equation
[H-].[Na+].[C:3]([C:7]1[C:8](=[O:25])[CH2:9][CH:10]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=3[CH:24]=2)[CH2:11][C:12]=1[OH:13])(=[O:6])[CH2:4][CH3:5].[CH2:26](Br)[CH:27]=[CH2:28]>CCCCCC>[C:3]([C:7]1[C:8](=[O:25])[CH2:9][CH:10]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][C:20](=[O:23])[N:19]([CH2:28][CH:27]=[CH2:26])[C:18]=3[CH:24]=2)[CH2:11][C:12]=1[OH:13])(=[O:6])[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178458824HCID 178458824, compound

Product 1

HCID 178456565HCID 178456565, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Sixty percent sodium hydride in mineral oil 0.60 g (15 mmol NaH) was washed once with 15 mL of hexane, decanting via pipette. To this was added 1.6 g (5.1 mmol) of 2-propionyl-3-hydroxy-5-(3-oxo-(2H, 4H)-1,4-benzoxazin-6-yl)cyclohex-2-en-1-one in solid portions. The mixture was stirred at room temperature for 15 minutes, treated with 1.4 g (12 mmol) of allyl bromide and stirred at room temperature for 30 minutes. The mixture was poured into 100 mL of ice cold 0.2N HCl and extracted twice with 30 mL portions of a 5:1 ether-ethyl acetate mixture. The extracts were combined, washed with water, an aqueous NaCl solution, dried over MgSO4, filtered and the solvent evaporated off to give the crude product, as a yellow solid. Recrystallization from ethanol afforded the above-named product in a yield of 1.4 g (77 percent of theoretical). The product melted at 129°-131.5° C.; 1 H NMR (CDCl3): d1.10 (t, J=7 Hz, 3H, --CH3), 2.55-3.56 (m, 7H), 4.52-4.73 (m including s at 4.50 for OCH2, 4H, --NCH2), 5.12-5.42 (m, 2H, --CH=CH2), 5.70-6.15 (m, 1H, --CH=CH2), 6.82-7.10 (m, 3H, aromatic H's), 18.10 (broad s, 1H, enol O--H).

Workup

  1. customdecanting via pipette
  2. stirringstirred at room temperature for 30 minutes
  3. extractionextracted twice with 30 mL portions of a 5:1 ether-ethyl acetate mixture
  4. washwashed with water
  5. dry with materialan aqueous NaCl solution, dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated off

Sources & evidence

ORD record
ord-46e5e65b8a144d4eac5ff5acb4da277a
Source dataset
uspto-grants-1995_03
Patent number
US05399542

Reaction notes

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