Lithium iodide → (R)-(-)-3,4-Dihydro-2-(4-hydroxybenzyl)-2H-benzopyran

HRID 1464820노트

반응식

HRID 1464820 반응식
C[O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][C@H:8]2[CH2:13][CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[O:9]2)=[CH:5][CH:4]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C.C(OCC)(=O)C.Cl>[OH:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][C@H:8]2[CH2:13][CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[O:9]2)=[CH:5][CH:4]=1

참가 물질

6

반응물 2

HCID 66321Lithium iodideHCID 18653186(R)-(-)-3,4-Dihydro-2-(4-methoxybenzyl)-2H-benzopyran

생성물 1

HCID 18653185(R)-(-)-3,4-Dihydro-2-(4-hydroxybenzyl)-2H-benzopyran수율 94.9%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 79532,4,6-Trimethylpyridine용매HCID 8857Ethyl Acetate용매

실험 절차

(R)-(-)-3,4-Dihydro-2-(4-methoxybenzyl)-2H-benzopyran (812 mg, 3.2 mmol), and lithium iodide (750 mg, 5.6 mmol) were dissolved in 2,4,6-collidine (2 ml) and heated to reflux for 24 hours. The reaction mixture was cooled, diluted with ethyl acetate (20 ml) and 10% HCl (20 ml), and stirred for 10 minutes. The layers were separated and the aqueous portion was extracted with ethyl acetate (50 ml). The combined organics were washed with water (20 ml), brine (20 ml), and were dried (MgSO4). The solvent was removed in vacuo and the residue purified on silica gel using hexanes/ethyl acetate (3:1) as eluent to afford 730 mg of a colorless oil which crystallized upon standing, m.p. 60°-62° C.; [α]D -110.2° (c 1.0, MeOH); 1H NMR (300 MHz, CDCl3) δ1.7 (m, 1H), 2.0 (m, 1H), 2.7-2.8 (m, 3H), 3.1 (dd, 1H), 4.2 (m, 1H), 6.8 (m, 3H), 7.0-7.2 (m, 4H).

후처리

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. customThe layers were separated
  5. extractionthe aqueous portion was extracted with ethyl acetate (50 ml)
  6. washThe combined organics were washed with water (20 ml), brine (20 ml)
  7. dry with materialwere dried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customthe residue purified on silica gel

출처 및 근거

ORD 기록
ord-b7a102fb092c49b9ba6a755cf7e714a9
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306726

반응 노트

불러오는 중…