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Toluene → HCID 54776256, 화합물

HRID 2423458
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HRID 2423458 반응식
[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]
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7

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HCID 1140TolueneHCID 9357Potassium Sodium Tartrate2회HCID 21225700DiisobutylaluminumhydrideHCID 59709034Methyl 3-{[(1,1-dimethylethyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate

생성물 1

HCID 54776256HCID 54776256, 화합물수율 91%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ee6d1b69ae5841a1b5f94b1c9e4070b1
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960552B2

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