4-Hydroxybiphenyl → HCID 18379631, compound

HRID 2097566Notes

Reaction equation

HRID 2097566 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:14]([N:27]1[CH2:30][CH:29](O)[CH2:28]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(#N)C.CCOC(C)=O.CCCCCC>[CH:14]([N:27]1[CH2:30][CH:29]([O:13][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][CH:11]=2)[CH2:28]1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 18379631HCID 18379631, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Phenylphenol (8.51 g, 50 mmol), 1-benzhydrylazetidin-3-ol (11.97 g, 50 mmol) and triphenylphosphine (13.11 g, 50 mmol) were stirred in acetonitrile (250 mL) for 20 minutes at room temperature, until all the reagents were fully dissolved. Diisopropyl Azodicarboxylate (9.84 mL, 10.11 g, 50 mmol) was added dropwise. A white precipitate forms and the initial reaction is mildly exothermic. The yellow colour is immediately discharged. After 5 minutes, the reaction is heated to reflux temperature, whereupon the precipitate dissolved, and stirred at this temperature for 3.25 hours. The mixture was cooled to room temperature, and scratched with a spatula to induce crystallisation. The mixture was cooled on ice, and the solids collected by filtration. The solids were washed with further cold acetonitrile and dried thoroughly to give the ether (15.42 g, 79%) as a white powder; mp 141-142° C.; Rf 0.68 (2:1 hexane:EtOAc); LCMS retention time 2.57 mins, m/z 392.2 [M+H]+; 1H nmr (400 MHz; DMSO-d6) δ 7.60-7.52 (m, 4H), 7.46-7.39 (m, 6H), 7.31-7.26 (m, 5H), 7.19 (tt, 2H, J=7.2 and 2.0 Hz), 6.90 (d, 2H, J=8.8 Hz), 4.88 (app qn, 1H, J=5.6 Hz), 4.53 (s, 1H), 3.67-3.63 (m, 2H) and 3.02-2.98 (m, 2H).

Workup

  1. dissolutionwere fully dissolved
  2. customA white precipitate forms and the initial reaction
  3. temperaturethe reaction is heated
  4. temperatureto reflux temperature
  5. dissolutionwhereupon the precipitate dissolved
  6. customcrystallisation
  7. temperatureThe mixture was cooled on ice
  8. filtrationthe solids collected by filtration
  9. washThe solids were washed with further cold acetonitrile
  10. customdried thoroughly
  11. customto give the ether (15.42 g, 79%) as a white powder

Sources & evidence

ORD record
ord-da5696e9bd9a4be2908300bfa26fe0ed
Source dataset
uspto-grants-2013_05
Patent number
US08450346B2

Reaction notes

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