Toluene → [3-[(Cyclopentyloxy)methyl]-5-(1-methylethyl)-4-isoxazolyl]methanol

HRID 2423484Notes

Reaction equation

HRID 2423484 reaction equation
[CH:1]1([O:6][CH2:7][C:8]2[C:12]([C:13](OC3CCCC3)=[O:14])=[C:11]([CH:21]([CH3:23])[CH3:22])[O:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[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+]>C1COCC1>[CH:1]1([O:6][CH2:7][C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH:21]([CH3:23])[CH3:22])[O:10][N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 21225700Diisobutylaluminumhydride2×HCID 59321532Cyclopentyl 3-[(cyclopentyloxy)methyl]-5-(1-methylethyl)-4-isoxazolecarboxylate

Product 1

HCID 59321541[3-[(Cyclopentyloxy)methyl]-5-(1-methylethyl)-4-isoxazolyl]methanolYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopentyl 3-[(cyclopentyloxy)methyl]-5-(1-methylethyl) -4-isoxazolecarboxylate (0.093 g, 0.29 mmol) in THF (2.8 mL) was stirred in an ice bath as a 1.5M solution of diisobutylaluminum hydride in toluene (0.42 mL, 0.63 mmol) was added dropwise. The solution was allowed to stir at room temperature for 2 hours. The solution was cooled to 0° C. before an additional portion of diisobutylaluminum hydride (0.42 mL, 0.63 mmol) was added and the solution was allowed to stir at room temperature for one hour. A 10% aqueous solution of Rochelle's salt (30 mL) was added and the solution was allowed to stir for 20 hours. The solution was extracted with ethyl acetate and the organic layer was dried with MgSO4, filtered and concentrated. The residue was purified by chromatography (silica gel, hexane to 1:1 ethyl acetate:hexanes) to provide [3-[(cyclopentyloxy)methyl]-5-(1-methylethyl)-4-isoxazolyl]methanol (0.051 g, 74%). 1H NMR (400 MHz, DMSO-d6): δ 4.82 (t, J=5 Hz, 1H), 4.42 (s, 2H), 4.30 (d, J=5 Hz, 2H), 3.95 (m, 1H) 3.24 (septet, J=7 Hz, overlapping H2O), 1.64-1.55 (m, 6H), 1.46 (m, 2H), 1.21 (d, J=7 Hz, 6H).

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. stirringto stir at room temperature for one hour
  4. stirringto stir for 20 hours
  5. extractionThe solution was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography (silica gel, hexane to 1:1 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-b84645aab2054f86a68555558992d318
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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