Ammonium Chloride → HCID 18329461, compound

HRID 260813Notes

Reaction equation

HRID 260813 reaction equation
CO[C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:11]1[O:12]C(C)(C)CN=1.[CH:18]([Mg]Cl)([CH3:20])[CH3:19].CC[O:25]CC.[Cl-].[NH4+]>O1CCCC1>[CH:18]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:11]([OH:12])=[O:25])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 14860489HCID 14860489, compoundHCID 178467793HCID 178467793, compound

Product 1

HCID 18329461HCID 18329461, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A 500 mL round-bottom flask equipped with nitrogen purge, septum inlet, and magnetic stirring, was dried under an atmosphere of nitrogen and charged with 5 g (21.2 mmoles) of 2-(2,3-dimethoxyphenyl)-5,5-dimethyloxazoline (which was synthesized in a like manner according to EXAMPLE 10) and 100 mL of tetrahydrofuran. The solution was cooled to 10° C. and 58 mL of 2N isopropylmagnesium chloride/ether was added. The mixture was stirred at room temperature overnight and poured into a 1:1 mixture of saturated ammonium chloride and ice. The mixture was extracted twice with ether; the organic layers were combined, dried over magnesium sulfate, and the solvent was removed in vacuo to yield 5.3 g of a yellow oil. This was dissolved in 200 mL of 6N hydrochloric acid and heated at reflux for 8.5 hours. The mixture was extracted several times with ether, and the combined organic phases were dried over sodium sulfate. The solvent was removed in vacuo to yield 4.6 g of oil which crystallized on standing. 1H NMR (200 MHz, CDCl3), δ=7.29 (1H, dd, 1.5, 7.5 Hz), 7.21 (1H, t, 7.5 Hz), 7.01 (1H, dd, 1.5, 7 Hz), 3.85 (3H, s), 3.65 (1H, m), 1.37 (6H, d, 7 Hz) ppm.

Workup

  1. customA 500 mL round-bottom flask equipped with nitrogen
  2. custompurge
  3. customseptum inlet, and magnetic stirring, was dried under an atmosphere of nitrogen
  4. customwas synthesized in a like manner
  5. extractionThe mixture was extracted twice with ether
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-51583be7149b4ea7aa7cb4763026b5f9
Source dataset
uspto-grants-1996_06
Patent number
US05530028

Reaction notes

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