Pyridine → HCID 15661461, compound

HRID 1707987Notes

Reaction equation

HRID 1707987 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 sol'n, 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-088838e9634e4e9d919a7cbba2bbcce8
Source dataset
uspto-grants-1994_10
Patent number
US05356889

Reaction notes

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