Tetrabutylammonium Fluoride → HCID 22285052, compound

HRID 1061874Notes

Reaction equation

HRID 1061874 reaction equation
[Si]([O:8][C:9]1[C:10]([CH3:45])=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([C:21]1[N:22]=[CH:23][N:24]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:25]=1)=[O:20])[CH:13]=[CH:12]2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:45][C:10]1[C:11]2[C:16](=[CH:15][C:14]([C:19]([C:21]3[N:22]=[CH:23][N:24]([C:26]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:25]=3)=[O:20])=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[OH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22285045HCID 22285045, compound

Product 1

HCID 22285052HCID 22285052, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(6-tert-Butyldimethylsilyloxy-5-methyl-2-naphthyl)(1-trityl-1H-imidazol-4-yl)methanone (30.0 g) was dissolved in THF (200 mL) and tetrabutylammonium fluoride (14.9 g) was added. The mixture was stirred at room temperature for 18 hrs. and the solvent was evaporated. Water was added to the residue and the mixture was extracted with ethyl acetate. The extracted layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with diisopropyl ether and dried to give the title compound (22.4 g) as pale-orange crystals.

Workup

  1. customand the solvent was evaporated
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extracted layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washThe residue was washed with diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-92bb3cc1cb5442928ad2be54d29560ec
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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