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

HRID 480357

반응식

HRID 480357 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 110304141,3-Benzodioxole-5-propanol수율 83.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1195e017ce5a4ed789bd312bccc4eb92
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649657B2

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