Benzophenone → HCID 118324209, compound

HRID 2274372Notes

Reaction equation

HRID 2274372 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C@:9]23[C:12]4[C:18]5[CH2:19][C@H:3]1[C@H:4]2[CH2:5][CH2:6][C@H:7]([OH:21])[C@H:8]3[O:14][C:13]=4[C:15]([OH:20])=[CH:16][CH:17]=5.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.COCCOC>[OH:20][C:15]1[C:13]2[O:14][C@@H:8]3[C:7](=[O:21])[CH2:6][CH2:5][C@H:4]4[C@:9]53[CH2:10][CH2:11][N:2]([CH3:1])[C@H:3]4[CH2:19][C:18]([C:12]=25)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 3102BenzophenoneHCID 23665647Potassium tert-butoxideHCID 118324254HCID 118324254, compound

Product 1

HCID 118324209HCID 118324209, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 26 (8 mg, 0.028 mmol) and benzophenone (10.2 mg, 0.056 mmol) in a mixture of toluene (1 mL) and DME (1 mL) was added potassium tert-butoxide (18 mg, 0.16 mmol) at room temperature. The resulting reaction mixture was heated at 85° C. for 8 hours and then the solvent was evaporated under reduced pressure to obtain the crude reaction mixture, which was purified by column chromatography on silica gel using [CH2Cl2/MeOH (95:5)→CH2Cl2/MeOH (90:10)] as eluent to provide 4 (3.5 mg, 0.012 mmol, 44%) as a white solid along with unreacted starting material 26 (4 mg, 0.014 mmol, 53%). The physical and spectral properties of 4 were matched with those given in the literature.7

Workup

  1. customThe resulting reaction mixture
  2. customthe solvent was evaporated under reduced pressure
  3. customto obtain the crude
  4. customreaction mixture, which
  5. customwas purified by column chromatography on silica gel using [CH2Cl2/MeOH (95:5)→CH2Cl2/MeOH (90:10)] as eluent

Sources & evidence

ORD record
ord-4c41ba7b83c840839225174016268cf4
Source dataset
uspto-grants-2015_09
Patent number
US09126965B1

Reaction notes

Loading…