4-tert-Butylphenol → HCID 11553465, compound

HRID 1173385Notes

Reaction equation

HRID 1173385 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]1([CH2:23][N:24]([CH2:37][CH2:38][OH:39])[C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:36])([F:35])[F:34])[CH:26]=2)[CH2:22][CH2:21]1.[C:40]([C:44]1[CH:49]=[CH:48][C:47](O)=[CH:46][CH:45]=1)([CH3:43])([CH3:42])[CH3:41].C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.C(=O)([O-])[O-]>C(Cl)Cl>[CH:20]1([CH2:23][N:24]([CH2:37][CH2:38][O:39][C:47]2[CH:48]=[CH:49][C:44]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:45][CH:46]=2)[C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:35])([F:36])[F:34])[CH:26]=2)[CH2:21][CH2:22]1

Participants

7

Reactant 5

HCID 73934-tert-ButylphenolHCID 11776TriphenylphosphineHCID 19660Carbonate IonHCID 5387121Dibenzyl azodicarboxylateHCID 11369616HCID 11369616, compound

Product 1

HCID 11553465HCID 11553465, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of polymer-supported triphenylphosphine (0.23 g, ca. 3 mmol/g, ca. 0.70 mmol) in CH2Cl2 was added 4-[(cyclopropylmethyl)(2-hydroxyethyl)amino]-2-(trifluoromethyl)benzonitrile (0.100 g, 0.35 mmol) and 4-tert-butylphenol (0.105 g, 0.70 mmol). The mixture was shaken for 10 min, a solution of DBAD (0.121 g, 0.525 mmol) in CH2Cl2 (0.5 mL) was added, and shaking was continued overnight. Solids were removed by filtration and the filtrate was shaken with polymer-supported carbonate (0.50 g, ca. 2.9 mmol/g, ca. 1.5 mmol CO32−) for 4 h. Solids were removed by filtration, the filtrate was treated with TFA (1 mL) for 1 h and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.0847 g of the title compound as a colorless gum: 1H NMR (300 MHz, CDCl3) δ 7.58 (d, J=8.8 Hz, 1H), 7.29 (app. d, J=8.8 Hz, 2H), 7.11 (d, J=2.4 Hz, 1H), 6.90 (dd, J=8.8, 2.5 Hz, 1H), 6.78 (app. d, J=8.7 Hz, 2H), 4.14 (t, J=5.8 Hz, 2H), 3.89 (t, J=5.6 Hz, 2H), 3.39 (d, J=6.2 Hz, 2H), 1.29 (s, 9H), 1.14-0.99 (m, 1H), 0.69-0.59 (m, 2H), 0.36-0.27 (m, 2H); MS (APCI) m/z 417 (M+1).

Workup

  1. stirringshaking
  2. waitwas continued overnight
  3. customSolids were removed by filtration
  4. customSolids were removed by filtration
  5. additionthe filtrate was treated with TFA (1 mL) for 1 h
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-1605cf83c4ef4f7cb4dce9089183ce7a
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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