Pyridine → HCID 15661461, compound

HRID 1885384Notes

Reaction equation

HRID 1885384 reaction equation
[OH:1][CH2:2][C:3]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]([C:17]([CH3:19])=[O:18])[CH:4]=1.N1C=CC=CC=1.[CH2:26]([O:29][C:30](Cl)=[O:31])[CH:27]=[CH2:28]>C1COCC1.C(Cl)Cl>[CH2:26]([O:29][C:30]([O:1][CH2:2][C:3]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]([C:17]([CH3:19])=[O:18])[CH:4]=1)=[O:31])[CH:27]=[CH2:28]

Participants

6

Reactant 3

HCID 1049PyridineHCID 18052Allyl chloroformateHCID 15661460HCID 15661460, compound

Product 1

HCID 15661461HCID 15661461, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxymethyl-3-methylcarbonyl-9-fluorenone (135 mg) was dissolved in THF (4 ml), cooled to 0° C. under N2. Pyridine (51 μl, 1.2 eq) was added followed by allyloxycarbonyl chloride (70 μl, 1.2 eq). The reaction mixture was allowed to stir overnight allowing it to come to room temperature. The reaction mixture was diluted with methylene chloride, washed with water, sat'd NaCl solution, dried and evaporated. The product was purified by preparative tlc (80 mg).

Workup

  1. customto come to room temperature
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe product was purified by preparative tlc (80 mg)

Sources & evidence

ORD record
ord-c73522d6a0374f9f97c8b04982035d75
Source dataset
uspto-grants-1992_09
Patent number
US05144028

Reaction notes

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