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

HRID 2423484ノート

反応式

HRID 2423484 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b84645aab2054f86a68555558992d318
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

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