Tetrabutylammonium Fluoride → HCID 18367261, compound

HRID 1741399Notes

Reaction equation

HRID 1741399 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:36][C:37]1[CH:38]=[C:39]([CH:64]=[CH:65][CH:66]=1)[CH2:40][CH:41]1[CH2:45][C:44](=[O:46])[O:43][CH:42]1[C:47]1[O:48][C:49]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[C:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[N:51]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1>[C:52]1([C:50]2[N:51]=[C:47]([CH:42]3[CH:41]([CH2:40][C:39]4[CH:64]=[CH:65][CH:66]=[C:37]([OH:36])[CH:38]=4)[CH2:45][C:44](=[O:46])[O:43]3)[O:48][C:49]=2[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18367371HCID 18367371, compound

Product 1

HCID 18367261HCID 18367261, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (THF) (0.75 ml) was added to a solution of 3-[3-(tert-butyldiphenylsilyloxy)benzyl]-2-(4,5-diphenyl-2-oxazolyl)-5-oxotetrahydrofuran (0.26 g) in THF (0.75 ml) at room temperature. The resulting mixture was stirred at the same temperature for 5 hours and partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 2-(4,5-diphenyl-2-oxazolyl)-3-(3-hydroxybenzyl)-5-oxotetrahydrofuran (133 mg) as a colorless oil. (+) APCI-MS (m/z): 412 (M+ +1) IR (Nujol): 3340, 1770, 1590 cm-1NMR (CDCl3, δ): 2.30-3.26 (4H, m), 3.35-3.47 (1H, m), 5.22 and 5.31 (1H, each d, J=18.2 and 6.1 Hz, respectively), 6.53-6.68 (2H, m), 7.12-7.65 (13H, m)

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-8d6ab5ff82404a2aa865cf49f3d43871
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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