Hydrochloric Acid → HCID 67325684, compound

HRID 1257584Notes

Reaction equation

HRID 1257584 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][C:7](=[O:19])[CH2:8][CH:9]1[CH2:14][CH2:13][C:12]([O:15]CC)=[CH:11][C:10]1=O.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1COCC1.CCCCCCC.O>[CH3:1][O:2][C:3]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][C:7](=[O:19])[CH2:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11]=[CH:10]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 67322634HCID 67322634, compound

Product 1

HCID 67325684HCID 67325684, compoundYield 98.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(2,4-Dimethoxy-benzyl)-2-(4-ethoxy-2-oxo-cyclohex-3-enyl)-acetamide (549 mg, 1.58 mmol) in THF (10 mL) at −78° C. was added 1.0M of diisobutylaluminum hydride in heptane (2.0 mL). The reaction mixture was then stirred at 0° C. for one hour. 5 M of hydrogen chloride in water (2.0 mL) was added and the reaction mixture stirred at room temperature for 30 minutes. The reaction mixture was then partitioned between water and ethyl acetate, and the organic layer dried with brine and magnesium sulfate, filtered, and evaporated in vacuo to yield 471.8 mg (98%) of N-(2,4-Dimethoxy-benzyl)-2-(4-oxo-cyclohex-2-enyl)-acetamide which was carried forward without purification. LCMS (Method E, ESI): RT=1.23 min, m+H=304.2; 1H NMR (400 MHz, CDCl3) δ: 7.19 (d, J=8.1 Hz, 1H), 6.84 (ddd, J=10.2, 2.6, 1.3 Hz, 1H), 6.45 (dt, J=8.2, 2.2 Hz, 2H), 5.97 (dd, J=10.2, 2.1 Hz, 1H), 5.88 (s, 1H), 4.38 (d, J=5.7 Hz, 2H), 3.83 (s, 3H), 3.80 (s, 3H), 3.02 (s, 1H), 2.51-2.36 (m, 2H), 2.36-2.27 (m, 1H), 2.23 (dd, J=14.5, 7.6 Hz, 1H), 2.19-2.08 (m, 1H), 1.76-1.62 (m, 1H).

Workup

  1. stirringthe reaction mixture stirred at room temperature for 30 minutes
  2. customThe reaction mixture was then partitioned between water and ethyl acetate
  3. dry with materialthe organic layer dried with brine and magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-de675e2191aa4df9bdfbd2020a21cd99
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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