Triethylamine → HCID 54270134, compound

HRID 543640Notes

Reaction equation

HRID 543640 reaction equation
[OH:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([CH3:16])[CH:11]=3)[C:6]=2[CH:5]=[C:4]([CH3:17])[CH:3]=1.C(N(CC)CC)C.[CH3:25][P:26](Cl)(=[O:36])[O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[CH3:35].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH3:25][P:26](=[O:36])([O:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([CH3:16])[CH:11]=3)[C:6]=2[CH:5]=[C:4]([CH3:17])[CH:3]=1)[O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[CH3:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 20460154HCID 20460154, compoundHCID 54343097HCID 54343097, compound

Product 1

HCID 54270134HCID 54270134, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

1-Hydroxy-3,7-dimethylfluoren-9-one (0.01 mole), triethylamine (0.011 mole) and toluene (75 ml) are charged into a glass reaction flask equipped with a stirrer, thermometer and addition funnel. The mixture is cooled to about -10° C. and a solution of O-(2-methyl-4-chlorophenyl) methylphosphonochloridate (0.011 mole) in toluene (25 ml) is slowly added with stirring. After the addition is completed the reaction mixture is allowed to slowly warm to room temperature and stirring is continued for a period of 24 hours. After this time the reaction mixture is filtered and the filtrate is stripped of solvent leaving a residue. This residue is subjected to column chromatography using mixtures of ethyl acetate and hexane as the eluant. The fractions containing product are combined and stripped of solvent to yield the desired product O-(2-methyl-4-chlorophenyl) O-(3,7-dimethylfluoren-9-one-1-yl) methylphosphonate.

Workup

  1. customequipped with a stirrer
  2. additionthermometer and addition funnel
  3. additionAfter the addition
  4. temperatureto slowly warm to room temperature
  5. stirringstirring
  6. filtrationAfter this time the reaction mixture is filtered
  7. customleaving a residue
  8. additionThe fractions containing product

Sources & evidence

ORD record
ord-473cea0c4fc14914a2357e8fd610834a
Source dataset
uspto-grants-1984_05
Patent number
US04447420

Reaction notes

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