Imidazole → 2-tert-Butyldimethylsilyloxy-9H-fluoren-9-one

HRID 725700

Reaction equation

HRID 725700 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([O:21]C)=O)[CH:13]=[CH:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1[CH:27]=[CH:26]N=C1.OC1C=CC2C3C(=CC=CC=3)C(=O)C=2C=1.[Si](Cl)(C(C)(C)C)(C)C>CN(C=O)C>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:16]2[C:15]3[C:14](=[CH:13][CH:12]=[CH:26][CH:27]=3)[C:19](=[O:21])[C:17]=2[CH:18]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 813862-Hydroxyfluoren-9-oneHCID 14645564Methyl 6-tert-butyldimethylsilyloxy-2-naphthoate

Product 1

HCID 146455782-tert-Butyldimethylsilyloxy-9H-fluoren-9-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The procedure for this reaction was the same as described above for methyl 6-tert-butyldimethylsilyloxy-2-naphthoate. A solution of imidazole (0.5 g, 7.4 mmol) in 2 mL of dry DMF was added to a solution of 2-hydroxy-9-fluorenone (Aldrich, 0.55 g, 2.8 mmol) and tert-butyldimethylsilyl chloride (0.5 g, 3.3 mmol) in 5 ML of dry DMF to give after workup 0.74 g (84%) of a yellow oil: 1H NMR (CDCl3) delta 7.612-6.891 (m, 7H), 0.994 (s, 9H), 0.224 (s, 6H); 13C NMR (CDCl3 delta 193.69, 157.04, 144.87, 137.52, 136.04, 134.73, 134.50, 127.92, 125.59, 124.28, 121.24, 119.56, 116.22, 25.60, 18.18, -4.46. ##STR34##

Sources & evidence

ORD record
ord-f05675d3ecbf47c5be51fa004f525139
Source dataset
uspto-grants-1998_01
Patent number
US05707559

Linked notes

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