Aluminium lithium hydride → HCID 11244656, 화합물

HRID 229284노트

반응식

HRID 229284 반응식
[C:1]1(=[C:8]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17](OCC)=[O:18])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1(=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=2)[C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86613511HCID 86613511, 화합물

생성물 1

HCID 11244656HCID 11244656, 화합물수율 86.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cold (5° C.) solution of ethyl ({4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}oxy)acetate (190) (0.200 g, 0.53 mmol) in THF (10 mL) was added 1 M solution of LiAlH4 (1.3 mL, 2.5 mmol). The reaction mixture was stirred at that temperature for 0.5 h. Reaction mixture was quenched with EtOAc (5 mL) and stirred for an additional 10 min before pouring into 20% aqueous HCl (50 ml). The reaction mixture was extracted with EtOAc (3×50 mL) and the combined organics washed with brine (1×25 ml), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using hexanes and EtOAc (4:1 to 3:2) as an eluent to afford 155 mg (86%) of compound 224 as a white solid. 1H NMR (300 MHz, CD3OD): δ 7.04 (d, J=8.7 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 6.70 (d, J=8.4 Hz, 2H), 4.03 (t, J=5.1 Hz, 2H), 3.86 (t, J=5.1 Hz, 2H), 2.32 (d, J=4.5 Hz, 4H), 1.60 (br s, 8H). LCMS (ESI): m/z 337 (M−H)−.

후처리

  1. customReaction mixture
  2. customwas quenched with EtOAc (5 mL)
  3. stirringstirred for an additional 10 min
  4. additionbefore pouring into 20% aqueous HCl (50 ml)
  5. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
  6. washthe combined organics washed with brine (1×25 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-3463287e9131412ab2beffbc58dffe8e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560589B2

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