2-Ethylphenol → HCID 21895261, compound

HRID 720777Notes

Reaction equation

HRID 720777 reaction equation
[OH:1][CH2:2][CH:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1O)[CH3:36].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[O:1][CH2:2][CH:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4])[CH3:36]

Participants

6

Reactant 4

HCID 69972-EthylphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6000202-(2-Hydroxy-1-methylethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 21895261HCID 21895261, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.0 g (24.4 mmol) of 2-(2-hydroxy-1-methylethyl)-1H-isoindole-1,3(2H)-dione (Y. Becker, A. Eisenstadt, J. K. Stille, J. Org. Chem., 1980, 45, 2145) and triphenylphosphine (7.00 g, 27.0 mmol) in 40 mL of dry tetrahydrofuran was stirred at 20° C. for 1 h. To the solution was added 2-ethylphenol (3.90 g, 32.0 mmol) and diethyl azodicarboxylate (5.0 mL, 32.0 mmol) and the solution was stirred an additional 40 h. The reaction mixture was concentrated in vacuo and the residue was diluted in diethyl ether and washed with water and brine. The organic layer was concentrated in vacuo and the crude product was purified by flash silica chromatography using 5% ethyl acetate/hexanes solution as eluent to give 3.0 g (40%) of 2-[2-(2-ethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione as a colorless oil: 1H NMR (CDCl3) δ 0.96 (t, 3H), 1.60 (d, 3H), 2.40 (m, 2H), 4.18 (dd, 1H), 4.48 (t, 1H), 4.84 (m, 1H), 6.80 (m, 1H), 6.90 (m, 1H), 7.10 (m, 2H), 7.70 (m, 2H), 7.84 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted in diethyl ether
  3. washwashed with water and brine
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe crude product was purified by flash silica chromatography

Sources & evidence

ORD record
ord-0217062cf12b49cb9b030b4613b1060c
Source dataset
uspto-grants-2006_11
Patent number
US07135585B2

Reaction notes

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