Acetyl chloride → HCID 21706132, compound

HRID 1594561Notes

Reaction equation

HRID 1594561 reaction equation
[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH:15]=[O:16])=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26]>C1COCC1>[C:25]([O:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH:15]=[O:16])=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21706134HCID 21706134, compound

Product 1

HCID 21706132HCID 21706132, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1.53 g (6.83 mmol) of 4-hydroxy-7-formyl-fluoren-9-one, prepared in Step G of Prepartive Example 12, in 25 mL THF at 0° C. was added 1.24 mL (8.88 mmol) of triethylamine and 0.58 mL (8.2 mmol) of acetyl chloride. The mixture was stirred further for 0.5 hour and then partitioned between EtOAc, ice, 1N HCl, and brine. The organic phase was separated, washed with brine, dried over Na2SO4, filtered, evaporated, and dried in vacuo. Purification by chromatography on silica gel using methylene chloride as eluant gave 1.46 g of the title compound.

Workup

  1. custompartitioned between EtOAc, ice, 1N HCl, and brine
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried in vacuo
  8. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-2fffbb79e7a0469d940f8aae0ede0354
Source dataset
uspto-grants-2001_09
Patent number
US06284753B1

Reaction notes

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