Aluminium lithium hydride → HCID 11244656、化合物

HRID 1716135ノート

反応式

HRID 1716135 の反応式
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[C:21]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:21]1(=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][OH:3])=[CH:8][CH:9]=2)[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 86613511HCID 86613511、化合物

生成物 1

HCID 11244656HCID 11244656、化合物収率 86.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-71a8704c8fc54b98bbc04388bc723be1
出典データセット
uspto-grants-2010_09
特許番号
US07799828B2

反応ノート

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