4-Isopropylphenol → HCID 9948092, compound

HRID 2120253Notes

Reaction equation

HRID 2120253 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][C:51](O)=[CH:50][CH:49]=1)([CH3:47])[CH3:46]>O1CCCC1>[CH:45]([C:48]1[CH:53]=[CH:52][C:51]([O:32][CH2:33][CH2:34][C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH2:37][C:38](=[O:44])[NH:39]3)=[CH:50][CH:49]=1)([CH3:47])[CH3:46]

Participants

6

Reactant 4

HCID 74654-IsopropylphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9948092HCID 9948092, compoundYield 37.2%

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 4-isopropylphenol (1.36 g, 10 mmol). The mixture was stirred at room temperature for one day and the solvent was evaporated. The residue was chromatographed on silica gel eluting with ethyl acetate:hexane 2:8 to give 1.1 g (37%) of 4-[2-(4-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one as a light yellow solid.

Workup

  1. stirringThe mixture was stirred at room temperature for one day
  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-d9adf9d433a24d2f8af8a57a40a1dfcd
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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