Benzyl Alcohol → HCID 67520233, compound

HRID 1925254Notes

Reaction equation

HRID 1925254 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](C(O)=O)[CH:6]=[CH:5]2.C[C@H]1[C@]2(O)[C@H]3[C@](O)(CC(COC(C)=O)=C[C@H]2[C@@H]2C(C)(C)[C@]2(O[C:44](CC2C=CC=CC=2)=[O:45])C1)C(=O)C(C)=C3.CC[N:55](CC)CC.[CH2:60]([OH:67])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>C1(C)C=CC=CC=1>[CH2:60]([O:67][C:44](=[O:45])[NH:55][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([OH:1])[C:3]=2[CH3:15])[CH:8]=1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 303482112-Deoxyphorbol 13-phenylacetate 20-acetateHCID 20736964HCID 20736964, compound

Product 1

HCID 67520233HCID 67520233, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture containing 6-hydroxy-5-methyl-naphthalene-2-carboxylic acid (3.42 g, 12.7 mmol), was added dppa (3 mL, 14.0 mmol) and Et3N (3.5 mL, 25.4 mmol) in 50 mL of toluene. After stirring for 10 min, benzyl alcohol (3.9 mL, 38.1 mmol) was added to the mixture and heated at reflux for 4 h. The crude was purified by silica-gel column chromatography in EtOAc/Hexanes to give the titled compound as brown solid. MS (ESI neg. ion) m/z: 306 (M−H). Mass Calc'd for C19H17NO3: 307.12.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. customThe crude was purified by silica-gel column chromatography in EtOAc/Hexanes

Sources & evidence

ORD record
ord-09acf1613c154dd1889c2c04514896ba
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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