Tetrabutylammonium Fluoride → HCID 10459476, compound

HRID 2231887Notes

Reaction equation

HRID 2231887 reaction equation
[O:1]1[C:5]([CH:6]([C:23]2[O:24][CH:25]=[C:26]([CH:28]([O:58][Si](CCCC)(C)C)[CH2:29][CH:30]([O:50][Si](CCCC)(C)C)[CH:31]([O:42][Si](CCCC)(C)C)[CH:32]([O:34][Si](CCCC)(C)C)[CH3:33])[N:27]=2)[O:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:4][N:3]=[CH:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:1]1[C:5]([CH:6]([C:23]2[O:24][CH:25]=[C:26]([CH:28]([OH:58])[CH2:29][CH:30]([OH:50])[CH:31]([OH:42])[CH:32]([OH:34])[CH3:33])[N:27]=2)[O:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53756246HCID 53756246, compound

Product 1

HCID 10459476HCID 10459476, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-[1-(oxazol-5-yl)-1-(tetradecanoyloxy)methyl]-4-[1,3,4,5-tetra(t-butyldimethylsilyloxy) hexyl]oxazole (8, 1.5 g, 1.5 mmol) in THF (100 mL) is added tetrabutylammonium fluoride (0.4 g, 1.5 mmol) in THF (1 mL). After five hours, the solvent is removed, water added, and the product extracted into ethyl acetate. Evaporation and purification bys ilica gel chromatography yields 2-[1-(oxazol-5-yl)-1-(tetradecanoyloxy) methyl]-4-(1,3,4,5-tetrahydroxyhexyl)oxazole (1, bengazole A).

Workup

  1. customthe solvent is removed
  2. additionwater added
  3. extractionthe product extracted into ethyl acetate
  4. customEvaporation and purification bys ilica gel chromatography

Sources & evidence

ORD record
ord-9c1ca7341139490789af27ef33d7725f
Source dataset
uspto-grants-1988_11
Patent number
US04785012

Reaction notes

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