[4-(Phenoxymethyl)phenyl]acetic acid → HCID 66578029、化合物

HRID 533575ノート

反応式

HRID 533575 の反応式
[O:1]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][OH:17])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 12832053[4-(Phenoxymethyl)phenyl]acetic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 66578029HCID 66578029、化合物収率 174%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a flask containing [4-(phenoxymethyl)phenyl]acetic acid (1.0 g, 4.13 mmol), in THF (20 mL) under external ice cooling was added a 1.0M sol of LiAlH4 in THF (8.3 mL, 8.3 mmol) (effervescence noted). The reaction mixture was stirred for three hours under ice cooling, then allowed to stir at room temperature for 48 hours. The reaction mixture was quenched with water (4.1 mL) and 1N NaOH (24 mL) then extracted into EtOAc (200 mL). The organic layer was washed with brine (150 mL). The organics were dried over Na2SO4, filtered and concentrated in vacuo to furnish 1.64 g of the title compound as a white solid (174%), containing aluminum salt impurities. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.90 (t, J=6.64 Hz, 2H) 3.88 (t, J=6.44 Hz, 2H) 5.05 (s, 2H) 6.93-7.02 (m, 3H) 7.22-7.36 (m, 4H) 7.40 (d, J=8.20 Hz, 2H).

後処理

  1. stirringto stir at room temperature for 48 hours
  2. customThe reaction mixture was quenched with water (4.1 mL) and 1N NaOH (24 mL)
  3. extractionthen extracted into EtOAc (200 mL)
  4. washThe organic layer was washed with brine (150 mL)
  5. dry with materialThe organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-33eb44cf00324717812beb3e1d87c4f9
出典データセット
uspto-grants-2014_10
特許番号
US08853258B2

反応ノート

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