Ammonium Chloride → HCID 54287875, compound

HRID 2379547Notes

Reaction equation

HRID 2379547 reaction equation
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].CC([Si](C)(C)[O:24][C:25]1[CH:26]=[C:27]([CH:31]([CH2:36][C:37]2[O:38][C:39]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[C:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[N:41]=2)[C:32]([O:34][CH3:35])=[O:33])[CH:28]=[CH:29][CH:30]=1)(C)C.[NH4+].[Cl-]>C1COCC1>[OH:24][C:25]1[CH:26]=[C:27]([CH:31]([CH2:36][C:37]2[O:38][C:39]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[C:40]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[N:41]=2)[C:32]([O:34][CH3:35])=[O:33])[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 18957380HCID 18957380, compound

Product 1

HCID 54287875HCID 54287875, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of nBu4NF (7.30 g, 28 mmol) in dry THF (27.9 mL) was added to a solution of methyl α-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-4,5-di phenyl-2-oxazolepropanoate (11.90 g, 23 mmol) in dry THF (250 mL) maintained at about -78° C. under an atmosphere of N2. After about 10 minutes, the mixture was poured onto saturated NH4Cl solution and extracted with CH2C2. The combined extracts were dried over Na2SO4, concentrated and the residue chromatographed on a column of silica gel. Elution with a mixture of Et2O and hexanes (1:1) gave methyl α- (3-hydroxyphenyl)-4,5-diphenyl-2-oxazolepropanoate (4.59 g, 47%).

Workup

  1. extractionextracted with CH2C2
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. customthe residue chromatographed on a column of silica gel
  5. washElution
  6. additionwith a mixture of Et2O and hexanes (1:1)

Sources & evidence

ORD record
ord-9d14a6718fa74cc2a58fce5bbfeb6055
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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