HCID 86720844, compound → HCID 86720845, compound

HRID 1482175Notes

Reaction equation

HRID 1482175 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:27]2[C:18](=[CH:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2.[CH3:29][Mg]Br.C([O:34][CH2:35][CH3:36])C>C1COCC1>[CH:15]1[C:16]2[C:11](=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:35]([OH:34])([CH3:36])[CH3:29])[C:27]3[C:18]([CH:17]=2)=[CH:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=3)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 86720844HCID 86720844, compoundHCID 178467822HCID 178467822, compound

Product 1

HCID 86720845HCID 86720845, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The methyl-2-(tetracen-5-yl)benzoate (2.58 g, 7.13 mmol) was dissolved in 200 mL of THF. A 3M methyl magnesium bromide-diethyl ether solution (7.84 mL, 23.5 mmol) was added dropwise in a nitrogen atmosphere under reflux at the boiling point and the mixture was reacted for 2 hours to obtain 2-(2-(tetracen-5-yl)phenyl)propan-2-ol at a yield of 81%. The 2-(2-(tetracen-5-yl)phenyl)propan-2-ol (2.09 g, 5.78 mmol) was added to a solvent mixture containing 100 mL of acetic acid and 20 mL of 37% hydrochloric acid and the mixture was reacted for 5 hours under reflux at the boiling point to synthesize Illustrative Compound A-8 at a yield of 36%.

Workup

  1. temperatureunder reflux at the boiling point
  2. customthe mixture was reacted for 2 hours

Sources & evidence

ORD record
ord-46db26ed01784d50907164cbe071ffeb
Source dataset
uspto-grants-2016_08
Patent number
US09412952B2

Reaction notes

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