Hydrochloric Acid → HCID 21973123, compound

HRID 11215Notes

Reaction equation

HRID 11215 reaction equation
[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([CH2:4][C:5]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:11]#N)[CH2:6][CH2:7]2)[O:2]1.CC(C[AlH]CC(C)C)C.Cl.C(=O)(O)[O-:30].[Na+]>C1(C)C=CC=CC=1>[CH2:1]1[CH2:10][O:9][C:3]2([CH2:8][CH2:7][CH2:6][C:5]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([CH:11]=[O:30])[CH2:4]2)[O:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 516892Sodium BicarbonateHCID 694237153-Ethylenedioxy-1-phenylcyclohexanecarbonitrile

Product 1

HCID 21973123HCID 21973123, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At −78° C., 3-ethylenedioxy-1-phenylcyclohexanecarbonitrile (1.66 g, 6.83 mmol) in toluene (20 mL) was added DIBAL-H (1.0 M solution in toluene, 8.88 mL) slowly and was stirred for 1 hr. The reaction mixture was warmed up to room temperature and was added 1N HCl solution (2.60 mL) and was stirred for 1 hr. Saturated sodium bicarbonate was added to quench the reaction and the organic layer was separated. The aqueous layer was extracted with dichloromethane 3 times and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum. The crude material was purified by filtering through a short silica gel pad with dichloromethane to give the title compound as a white sticky oil (1.43 g, 85% yield). 1H NMR (400 MHz, CDCl3) δ 1.32–1.40 (1H, m), 1.46–1.54 (1H, m), 1.72–1.86 (3H, m), 2.08 (1H, d, J=16 Hz), 2.59–2.67 (2H, m), 3.94–4.07 (4H, m), 7.15–7.36 (5H, m), 9.36 (1H, d, J=4 Hz).

Workup

  1. stirringwas stirred for 1 hr
  2. customto quench
  3. customthe reaction
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with dichloromethane 3 times
  6. dry with materialthe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude material was purified
  10. filtrationby filtering through a short silica gel pad with dichloromethane

Sources & evidence

ORD record
ord-11d6b4e2d7e343d0996c130ebd1192a0
Source dataset
uspto-grants-2006_08
Patent number
US07098203B2

Reaction notes

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