Tetrabutylammonium Fluoride → HCID 18367261, compound

HRID 380133Notes

Reaction equation

HRID 380133 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 1.0M 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.

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-32c9fddd2ea84fbc8a6bceb53e55c561
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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