Toluene → HCID 23113966, compound

HRID 2376267Notes

Reaction equation

HRID 2376267 reaction equation
[OH:1][CH2:2][CH:3]([C:13]1[C:18]([CH3:19])=CC(C)=C(C)C=1O)[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][CH:5]=1.[C:23]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:54]1([CH3:60])[CH:59]=CC=[CH:56][CH:55]=1>C1COCC1>[CH:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:3]2[C:13]3[C:18]([CH3:19])=[CH:56][C:55]([CH3:23])=[C:54]([CH3:60])[C:59]=3[O:1][CH2:2]2)=[CH:5][CH:6]=1)([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 23114180HCID 23114180, compound

Product 1

HCID 23113966HCID 23113966, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-hydroxy-1-(4-isopropylphenyl)ethyl)-3,5,6-trimethylphenol obtained in Reference Example 8 (7.85 g, 26.3 mmol) and triphenylphosphine (7.58 g, 28.9 mmol) in THF (60 mL) was added diethylazodicarboxylate (a 40% toluene solution 12.6 g, 28.9 mmol) with ice-cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was concentrated under reduced pressure to obtain the residue, which was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 5.70 g (yield 84%) of the title compound. Melting point: 48-49° C. (methanol).

Workup

  1. temperaturecooling
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customto obtain the residue, which
  4. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-e5944d3354a74808bde2b526b4000eb2
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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