2-Isopropylphenol → HCID 9796184, compound

HRID 2120230Notes

Reaction equation

HRID 2120230 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][CH2:33][CH2:34][C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][C:38](=[O:44])[NH:39]2.[CH:45]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1O)([CH3:47])[CH3:46]>O1CCCC1>[CH:45]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[O:32][CH2:33][CH2:34][C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][C:38](=[O:44])[NH:39]2)([CH3:47])[CH3:46]

Participants

6

Reactant 4

HCID 69432-IsopropylphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9796184HCID 9796184, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.58 mL, 10 mmol) was added to a solution of triphenylphosphine (2.62 g, 10 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.77 g, 10 mmol) followed by 2-isopropylphenol (1.36 mL, 10 mmol). The mixture was stirred at room temperature for 18 hours and the solvent was evaporated. The residue was chromatographed on silica gel eluting with ethyl acetate: hexane 2:8 to give 0.26 g (9%) of 4-[2-(2-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one as a light yellow solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. customthe solvent was evaporated
  3. customThe residue was chromatographed on silica gel eluting with ethyl acetate: hexane 2:8

Sources & evidence

ORD record
ord-3aaef9711ee14d14983f7334ea54ea16
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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