Methyl iodide → HCID 10377376, compound

HRID 1668437Notes

Reaction equation

HRID 1668437 reaction equation
[CH2:1]([Li])CCC.CCCCCC.[C:12]1([C:18]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:21]([CH3:29])[O:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CI.[NH4+].[Cl-]>C1COCC1>[C:12]1([C:18]2[C:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[C:21]([CH2:29][CH3:1])[O:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 99916735-Methyl-3,4-diphenylisoxazoleHCID 178418339Butyllithium

Product 1

HCID 10377376HCID 10377376, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium in hexane (2.19M, 0.213 mL, 0.4675 mmol) is added to 3,4-diphenyl-5-methylisoxazole (P10, 0.100 g, 0.425 mmol) in THF (5 mL) kept stirring at −78° C. in a nitrogen atmosphere. The reaction mixture obtained is kept stirring for 1 hour at −78° C. before adding CH3I (4.25 mmol). The reaction mixture is brought to ambient temperature and then blocked by adding an aqueous solution of NH4Cl. The two phases are separated and the aqueous phase is extracted three times with ethyl acetate. The combined organic extracts are dried over Na2SO4 and the solvent is then evaporated in a vacuum. The residue is subjected to column chromatography (silica gel, petroleum ether:ethyl acetate=10/1) and 3,4-diphenyl-5-ethylisoxazole is obtained with a yield of 75%. M.p. 85-87° C. (hexane), white crystals. FT-IR (KBr): 3029, 3005, 2923, 2848, 1625, 1596, 1493, 1467, 1437, 1410, 1327, 1282, 1210, 1011, 905, 771, 702 cm−1. 1H NMR (200 MHz, CDCl3, δ): 1.29 (t, 3H), 2.78 (q, 2H); 7.12-7.43 (m, 10H). 13C NMR (75 MHz, CDCl3, δ): 12.5, 19.7, 115.2, 127.9, 128.7, 128.9, 129.4, 129.5, 130.2, 130.7, 161.3, 171.4. GC-MS (70 eV) m/z (rel.int.): 249 [M+, 100], 234 (6), 221 (18), 220 (99), 194 (9), 193 (61), 192 (46), 165 (17), 115 (7), 103 (8), 89 (53), 77 (15), 63 (10), 51 (10).

Workup

  1. customThe reaction mixture obtained
  2. stirringis kept stirring for 1 hour at −78° C.
  3. customis brought to ambient temperature
  4. customThe two phases are separated
  5. extractionthe aqueous phase is extracted three times with ethyl acetate
  6. dry with materialThe combined organic extracts are dried over Na2SO4
  7. customthe solvent is then evaporated in a vacuum

Sources & evidence

ORD record
ord-d9608b4bf7c545939fd224aef7b5731f
Source dataset
uspto-grants-2011_08
Patent number
US07989450B2

Reaction notes

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