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Toluene → HCID 54776256, compound

HRID 2423458
Notes
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Reaction equation

HRID 2423458 reaction equation
[CH3:1][C:2]([O:5][CH2:6][C:7]1[C:11]([C:12](OC)=[O:13])=[C:10]([CH:16]([CH3:18])[CH3:17])[O:9][N:8]=1)([CH3:4])[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1.C(OCC)(=O)C>[CH3:4][C:2]([O:5][CH2:6][C:7]1[C:11]([CH2:12][OH:13])=[C:10]([CH:16]([CH3:18])[CH3:17])[O:9][N:8]=1)([CH3:1])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 9357Potassium Sodium Tartrate2×HCID 21225700DiisobutylaluminumhydrideHCID 59709034Methyl 3-{[(1,1-dimethylethyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate

Product 1

HCID 54776256HCID 54776256, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of methyl 3-{[(1,1-dimethylethyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate (21.5 g, 84.2 mmol) in tetrahydrofuran (250 mL) at 0° C. was added a 1.5 M solution of diisobutylaluminum hydride in toluene (185 mL, 278 mmol) slowly. The solution was allowed to warm slowly to ambient temperature overnight then was re-cooled to 0° C. and approximately 250 mL of Rochelle's salt was added dropwise followed by approximately 300 mL of ethyl acetate. An additional 250 mL of Rochelle's salt and 500 mL of ethyl acetate were added and the mixture was stirred at 0° C. for approximately 20 minutes and then at ambient temperature for approximately 4 hours. The mixture was filtered. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, concentrated, and purified by chromatography (silica gel, 20% ethyl acetate in hexanes) to afford [3-{[(1,1-dimethylethyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol (15.2 g, 91%). 1H-NMR (400 MHz, DMSO-d6) δ 4.76 (t, J=5 Hz, 1H), 4.39 (s, 2H), 4.32 (d, J=5 Hz, 2H), 3.24 (septet, J=7 Hz, 1H), 1.21 (d, J=7 Hz, 6H), 1.18 (s, 9H).

Workup

  1. temperaturethen was re-cooled to 0° C.
  2. waitat ambient temperature for approximately 4 hours
  3. filtrationThe mixture was filtered
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by chromatography (silica gel, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ee6d1b69ae5841a1b5f94b1c9e4070b1
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960552B2

Reaction notes

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