Phenol → HCID 89584978, compound

HRID 1501012Notes

Reaction equation

HRID 1501012 reaction equation
[OH:1][C@@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3].[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>O1CCCC1>[O:1]([C@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 6932349HCID 6932349, compound

Product 1

HCID 89584978HCID 89584978, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 4-(1-hydroxyethyl)benzoate (360 mg, 2 mmol) in anhydrous tetrahydrofuran (20 mL) was added phenol (188 mg, 2 mmol) and triphenylphosphine (524 mg, 2 mmol) at 0° C., then stirred for 1 hour, (E)-diisopropyl diazene-1,2-dicarboxylate (404 mg, 2 mmol) was added, then stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=4:1) to give (S)-methyl 4-(1-phenoxyethyl)benzoate (410 mg, 80%). LRMS (M+H+) m/z: calcd 256.11. found 256.

Workup

  1. stirringstirred at room temperature for 12 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=4:1)

Sources & evidence

ORD record
ord-22141782fd3945b591822f71845bdba2
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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