Tetrabutylammonium Fluoride → HCID 53965118, compound

HRID 1602968Notes

Reaction equation

HRID 1602968 reaction equation
[OH:1][C:2]1([C:15]2[C:16](=[O:52])[NH:17][C:18](=[O:51])[N:19]([CH:50]=2)[C@@H:20]2[O:49][C@H:39]([CH2:40][O:41][Si](C(C)(C)C)(C)C)[C@@H:30]([O:31][Si](C(C)(C)C)(C)C)[C@H:21]2[O:22][Si](C(C)(C)C)(C)C)[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.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:1][C:2]1([C:15]2[C:16](=[O:52])[NH:17][C:18](=[O:51])[N:19]([CH:50]=2)[C@@H:20]2[O:49][C@H:39]([CH2:40][OH:41])[C@@H:30]([OH:31])[C@H:21]2[OH:22])[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

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18394984HCID 18394984, compound

Product 1

HCID 53965118HCID 53965118, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of step (i) (6.56 g) was treated with a 1M solution of tetra-n-butyl ammonium fluoride in tetrahydrofuran (28.2 ml) and the mixture was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica-gel eluting with 10% methanol in ethyl acetate to give 5-(9-hydroxyfluoren-9-yl)uridine as a pale yellow solid (3.43 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica-gel
  3. washeluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-a72f52c5382242fdb99e8693f3dfa35b
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

Loading…