Diethyl Ether → HCID 15086709, compound

HRID 359355Notes

Reaction equation

HRID 359355 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5](OC(=O)C)[O:4][N:3]=1.[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:19]([O:21]CC)[CH3:20]>>[CH3:1][C:2]1[CH:6]=[C:5]([C:19]([OH:21])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:20])[O:4][N:3]=1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 15135545HCID 15135545, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 15086709HCID 15086709, compoundYield 89%

Procedure

To a solution of 3-methyl-5-acetoxy-isoxazole (14 g, 112 mM) in diethyl ether (400 mL) at 0° C., was added a 3M solution of phenylmagnesium bromide in diethyl ether (44.7 mL, 134 mM) dropwise. After the addition was complete, the reaction mixture was stirred for 30 minutes. When pH 7 buffer (100 mL) was added, the layers were separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give 3-methyl-5-(1-hydroxy-1-phenylethyl)-isoxazole as an amber oil (20.2 g, 89%) that was used without further purification. 1H NMR (CDCl3, 100 MHz): δ 7.40 (m, 5H), 6.0 (s, 1H), 2.38 (s, 3H), 1.87 (s, 3H).

Workup

  1. additionAfter the addition
  2. additionWhen pH 7 buffer (100 mL) was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with diethyl ether (2×75 mL)
  5. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9cc16545c359426299b51316a8948a87
Source dataset
uspto-grants-1991_03
Patent number
US05001126

Reaction notes

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