Water → Tropenol 9-hydroxyfluorene-9-carboxylate

HRID 1006427Notes

Reaction equation

HRID 1006427 reaction equation
[OH:1][C:2]1([C:15]([O:17]C)=[O:16])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[C@@:19]12([OH:28])[N:26]([CH3:27])[C@@H:23]([CH2:24][CH2:25]1)[CH2:22][CH:21]=[CH:20]2.[Na].O>C(#N)C>[C@@:19]12([OH:28])[N:26]([CH3:27])[C@@H:23]([CH2:24][CH2:25]1)[CH2:22][CH:21]=[CH:20]2.[OH:1][C:2]1([C:15]([O-:17])=[O:16])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

6

Reactant 4

HCID 962WaterHCID 267210Methyl 9-hydroxy-9H-fluorene-9-carboxylateHCID 5360545Sodium2×HCID 53629842Tropenol

Product 1

HCID 86593872Tropenol 9-hydroxyfluorene-9-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.4 g (0.056 mol) of methyl ester 3a, 11.65 g (0.084 mol) of tropenol, and 0.3 g of sodium are heated as a melt at 75 mbar for 4 hours over a bath of boiling water with occasional agitation. After cooling, the sodium residues are dissolved with acetonitrile, the solution is evaporated to dryness, and the residue is extracted with dichloromethane/water. The organic phase is washed with water, dried over magnesium sulfate (MgSO4), and the solvent is distilled off. The product is purified by recrystallization from diethyl ether. Yield: 11.40 g of white crystals (29% of theoretical yield).

Workup

  1. temperatureAfter cooling
  2. customthe solution is evaporated to dryness
  3. extractionthe residue is extracted with dichloromethane/water
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate (MgSO4)
  6. distillationthe solvent is distilled off
  7. customThe product is purified by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-7943abcd711d46c8a7614c9622070fa7
Source dataset
uspto-grants-2004_09
Patent number
US06790856B2

Reaction notes

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