Hydrochloric Acid → 1,3-Benzodioxole-5-propanol

HRID 480357

反応式

HRID 480357 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][C:18](O)=[O:19])=[CH:15][C:10]=2[O:9][CH2:8]1.Cl>C1COCC1>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][CH2:18][OH:19])=[CH:15][C:10]=2[O:9][CH2:8]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 648103-(Benzodioxol-5-yl)propionic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 110304141,3-Benzodioxole-5-propanol収率 83.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium aluminum hydride (1M in THF, 30 mL, 30 mmol) was added slowly to a solution of 3-benzo[1,3]dioxol-5-yl-propionic acid (5.83 g, 30 mmol) in THF (60 mL) at 0° C. The reaction was warmed to room temperature and was stirred for 2 h. The solution was added in portions to a mixture of ice (200 g) and concentrated HCl (2 mL). The product was extracted into EtOAc. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 6:4) provided the title alcohol (4.51 g). 1H NMR (400 MHz, CDCl3) δ 6.73-6.62 (m, 3H), 5.91 (s, 2H), 3.66 (t, 2H), 2.63 (t, 2H), 1.84 (m, 2H).

後処理

  1. extractionThe product was extracted into EtOAc
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (hexanes:EtOAc 6:4)

出典と根拠

ORDレコード
ord-1195e017ce5a4ed789bd312bccc4eb92
出典データセット
uspto-grants-2003_11
特許番号
US06649657B2

関連ノート

読み込み中…