4-tert-Butylphenol → HCID 18671362, compound

HRID 1057296Notes

Reaction equation

HRID 1057296 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([CH:26]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:27]2[CH2:30][CH:29]([OH:31])[CH2:28]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:38]([C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)([CH3:41])([CH3:40])[CH3:39].N(C(OCC)=O)=NC(OCC)=O>C(#N)C.O>[C:38]([C:42]1[CH:47]=[CH:46][C:45]([O:31][CH:29]2[CH2:30][N:27]([CH:26]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:28]2)=[CH:44][CH:43]=1)([CH3:41])([CH3:40])[CH3:39]

Participants

7

Reactant 4

HCID 73934-tert-ButylphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 18671362HCID 18671362, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine (13.11 g, 50.0 mmol) was added to a stirred solution of 1-(diphenylmethyl)-3-azetidinol (11.97 g, 50.0 mmol) and 4-tert-butylphenol (7.50 g, 50.0 mmol) in acetonitrile (200 mL). Diethyl azodicarboxylate (7.9 mL, 8.7 g, 50.0 mmol) was added dropwise to the solution with water cooling. The suspension was heated under reflux for 4 h, the solution allowed to cool and concentrated in vacuo. The gum was suspended in ether (200 mL), and the suspension was refrigerated overnight. The precipitated triphenylphosphine oxide was filtered off and washed with ether, and the combined filtrate and washings were concentrated. The solid residue was dissolved in dichloromethane (200 mL), and the solution was washed with 1-N sodium hydroxide (50 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was purified by chromatography [SiO2; ethyl acetate-hexane (1:4)] and triturated with cyclohexane to give the title compound (9.39 g, 51%) as a white solid, m.p. 126-127° C. Found: C, 83.9; H, 7.9; N, 3.75. C26H29NO require C, 84.1; H, 7.9; N, 3.8%.

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 4 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. filtrationThe precipitated triphenylphosphine oxide was filtered off
  6. washwashed with ether
  7. concentrationthe combined filtrate and washings were concentrated
  8. dissolutionThe solid residue was dissolved in dichloromethane (200 mL)
  9. washthe solution was washed with 1-N sodium hydroxide (50 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe crude product was purified by chromatography [SiO2; ethyl acetate-hexane (1:4)]
  13. customtriturated with cyclohexane

Sources & evidence

ORD record
ord-962e4b1dc68142d5b5a78a8191acbec1
Source dataset
uspto-grants-2003_02
Patent number
US06514961B1

Reaction notes

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