Ammonium Chloride → HCID 68959536, compound

HRID 2378076Notes

Reaction equation

HRID 2378076 reaction equation
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3([CH:27]=[O:28])[CH2:26][CH2:25]3)[O:15][N:14]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:31]([Mg]Br)[CH3:32].[Cl-].[NH4+]>O1CCCC1>[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3([CH:27]([OH:28])[CH2:31][CH3:32])[CH2:26][CH2:25]3)[O:15][N:14]=2)=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86613308HCID 86613308, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 68959536HCID 68959536, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarbaldehyde, which may be produced as in Example 172 (20.38 g) in 300 mL tetrahydrofuran under an N2 atmosphere is cooled to 0° C. Ethylmagnesium bromide (53.4 mL, 1.0 M/methyl tert-butyl ether) is added over approximately 15 minutes. The reaction is stirred at 0° C. for 1 hour, 10 minutes. Saturated ammonium chloride (˜600 mL) is added and the product is extracted into ethyl acetate two times. The combined organic extracts are washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material is purified by column chromatography (15% followed by 20% ethyl acetate/hexane) to obtain a viscous oil that partially solidified under house vacuum. The material is dried in a 50° C. vacuum oven for approximately 1 hour to give (±)-1-(1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-propan-1-ol as a waxy off-white solid.

Workup

  1. extractionthe product is extracted into ethyl acetate two times
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material is purified by column chromatography (15% followed by 20% ethyl acetate/hexane)
  7. customto obtain a viscous oil that
  8. customThe material is dried in a 50° C. vacuum oven for approximately 1 hour

Sources & evidence

ORD record
ord-ae15d68857424caea4e038cd41a91a19
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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