Ethyl Acetate → HCID 57565084, compound

HRID 1726864Notes

Reaction equation

HRID 1726864 reaction equation
[C:1]1([C:7]2([C:14]#N)[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=[O:30])C>C1(C)C=CC=CC=1>[C:1]1([C:7]2([CH:14]=[O:30])[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 57565080HCID 57565080, compound

Product 1

HCID 57565084HCID 57565084, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (Z)-1-phenylcyclohept-4-enecarbonitrile from step B in toluene (15 mL) at −78° C. was added diisobutylaluminum hydride (1.0 M solution in toluene, 4.88 mL), and the resulting solution was stirred at −78° C. for 2 h. Saturated ammonium chloride was added drop wise followed by ethyl acetate. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo to give the title compound. 1H NMR (400 MHz, CDCl3) δ 2.21 (6H, m), 2.37 (2H, m), 5.69 (2H, s), 7.30 (5H, m), and 9.38 (1H, s).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-8382a7b2cc7c4e14b73f69ad10661b3d
Source dataset
uspto-grants-2009_02
Patent number
US07494986B2

Reaction notes

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