Ammonia → HCID 70021403, compound

HRID 989611Notes

Reaction equation

HRID 989611 reaction equation
[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][CH2:21][C@H:20]4[C:11](=[CH:12][CH2:13][C:14]5[CH:15]=[C:16]([O:23][CH3:24])[CH:17]=[CH:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1.N.[Li].C(O)C>C1COCC1>[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:22][CH2:21][C@H:20]4[C:11](=[CH:12][CH2:13][C:14]5[CH2:15][C:16]([O:23][CH3:24])=[CH:17][CH2:18][C:19]=54)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 702EthanolHCID 3028194LithiumHCID 70022911HCID 70022911, compound

Product 1

HCID 70021403HCID 70021403, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-33 °C

Procedure

To a solution of the arene 1 (1.63 g, 5 mmol) in THF (25 mL) was condensed liquid ammonia (100 mL). Small pieces of freshly cut lithium wire (0.6 g, 86 mmol) were added over a period of 5 min at −50° C. The deep blue solution was stirred at −33° C. for 30 min and ethanol (100%, 10 mL) was added over a period of 10 min. The ammonia was allowed to evaporate and water (20 mL) was added. The biphasic mixture was transferred to a separatory funnel and extracted with ether (3×30 mL). The ether extracts were combined, washed with brine, dried over potassium carbonate and concentrated to afford a shiny white solid which was washed with ether (4×20 mL) to give the enol ether 2 (1.2 g, 73%).

Workup

  1. customto evaporate
  2. additionwater (20 mL) was added
  3. customThe biphasic mixture was transferred to a separatory funnel
  4. extractionextracted with ether (3×30 mL)
  5. washwashed with brine
  6. dry with materialdried over potassium carbonate
  7. concentrationconcentrated
  8. customto afford a shiny white solid which
  9. washwas washed with ether (4×20 mL)

Sources & evidence

ORD record
ord-2c11ddcf2d5d40e89b55bd043243e3ef
Source dataset
uspto-grants-2002_10
Patent number
US06458778B1

Reaction notes

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