Nitrogen → HCID 86723000, compound

HRID 1486212Notes

Reaction equation

HRID 1486212 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].N#N.[CH2:9]([O:16][CH2:17][CH2:18][CH:19]1[CH2:24]CC(=O)C[CH2:20]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH2:1]=[C:2]1[CH2:4][CH2:20][CH:19]([CH2:18][CH2:17][O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:24][CH2:3]1

Participants

5

Reactant 3

HCID 947NitrogenHCID 218796054-(2-Benzyloxyethyl)cyclohexanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86723000HCID 86723000, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (−78° C.) mixture of Ph3PCH2Br (5.42 g, 14.88 mmol) in THF (25 mL) was added KOtBu (1M in THF, 17.05 mL, 17.05 mmol) dropwise under N2. The resulting mixture was stirred at 0° C. for 1 h and warmed to rt for another 1.5 h. The reaction mixture was then cooled to −40° C., added a solution of 4-(2-(benzyloxy)ethyl)cyclohexanone (1.8 g, 7.75 mmol) in THF (15 mL) dropwise. The mixture was then stirred at rt overnight and quenched by brine, extracted with EtOAc, dried over Na2SO4. Purification by flash column chromatography (eluent: 20% EtOAc in hexanes to 30%) gave the titled product (1.77 g, 99%). LC/MC: 231.1 (MH)+.

Workup

  1. temperatureTo a cooled
  2. temperaturewarmed to rt for another 1.5 h
  3. temperatureThe reaction mixture was then cooled to −40° C.
  4. stirringThe mixture was then stirred at rt overnight
  5. customquenched by brine
  6. extractionextracted with EtOAc
  7. dry with materialdried over Na2SO4
  8. customPurification by flash column chromatography (eluent: 20% EtOAc in hexanes to 30%)

Sources & evidence

ORD record
ord-5010b36188cc4c849698890f0e3d508d
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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