Benzyl Alcohol → HCID 20077190, compound

HRID 1654946Notes

Reaction equation

HRID 1654946 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([CH2:16]C(O)=O)[CH2:10]2)=[O:5])[CH3:2].C([N:22]([CH2:25]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.[CH2:44]([OH:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([CH2:16][NH:22][C:25]([O:51][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:34])[CH2:10]2)[CH3:2]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18921505HCID 18921505, compound

Product 1

HCID 20077190HCID 20077190, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

11.2 g (42.8 mmol) of [5-(ethoxycarbonylmethyl)indan-2-yl]acetic acid and 6.5 ml (46.7 mmol) triethylamine were dissolved in 140 ml toluene, to which was added 14.1 g (51.4 mmol) of diphenylphosphorylazide, followed by stirring for 30 minutes at room temperature. Subsequently, 5.05 g (46.7 mmol) of benzyl alcohol was added and refluxed for 14 hours. After cooling, the reaction mixture was washed with 1N hydrochloric acid, water, 1N sodium hydroxide and water in this order and dried. The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform) to obtain 12.7 g colorless solid. Yield: 81%

Workup

  1. temperaturerefluxed for 14 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with 1N hydrochloric acid, water, 1N sodium hydroxide and water in this order
  4. customdried
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-604f71f14d974f84b78a440e5a10059a
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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