Sodium hydride → 1-Methoxy-4-((oct-7-en1-yloxy)methyl)benzene

HRID 1040325

반응식

HRID 1040325 반응식
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[H-].[Na+].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>CN(C=O)C>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8])=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 83203Oct-7-en-1-ol

생성물 1

HCID 584607981-Methoxy-4-((oct-7-en1-yloxy)methyl)benzene수율 49%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

A 250 mL round-bottom flask equipped with stir bar was charged with 7-octen-1-ol (1.20 mL, 7.80 mmol). Anhydrous DMF (60 mL) was added, and the solution was allowed to cool to 0° C. (ice-bath). Sodium hydride (2.40 g, 40.0 mmol) was added in portions, and the mixture was allowed to stir until gas evolution ceased. p-Methoxybenzyl chloride (2.1 mL, 16 mmol) was added by a syringe and the mixture was allowed to stir for 24 h. The reaction was quenched by addition of a saturated aqueous solution of sodium bicarbonate (100 mL), and washed with ethyl acetate (5×100 mL). The combined organic layers were washed with water (3×100 mL) to remove dmf, further washed in brine (1×50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The resulting yellow oil was purified by silica gel chromatography (96:4 hexanes:EtOAc), delivering 1-methoxy-4-((oct-7-en1-yloxy)methyl)benzene (946 mg, 3.81 mmol, 49.0% yield) as a colorless oil. IR (neat): 3074 (w), 2998 (m), 2929 (m), 2854 (w), 1640 (m), 1613 (w), 1586 (w), 1511 (m), 1463 (m), 1441 (w), 1361 (w), 1301 (m), 1245 (s), 1208 (w), 1172 (m), 1095 (s), 1036 (s), 995 (w), 909 (m), 819 (s), 755 (w), 727 (w), 707 (w), 637 (w), 571 (w), 513 (w), 418 (w); 1H NMR (400 MHz, CDCl3): δ 7.25 (2H, d, J=8.8 Hz), 6.87 (2H, d, J=8.4 Hz), 5.80 (1H, m), 4.98 (1H, dd, J=17.2, 2.0 Hz), 4.92 (1H, dd, J=10.0, 2.4 Hz), 4.42 (2H, s), 3.79 (3H, s), 3.43 (2H, t, J=6.6 Hz), 2.03 (2H, app q, J=6.9 Hz), 1.63-1.56 (2H, m), 1.41-1.27 (6H, m); 13C NMR (100 MHz, CDCl3): δ 159.2, 139.2, 130.9, 129.3, 114.3, 113.8, 72.6, 70.3, 55.3, 33.8, 29.8, 29.1, 29.0, 26.2; HRMS (ESI+) [M+NH4]+ calcd for C16H28NO2: 266.2120, found: 266.2130.

후처리

  1. customA 250 mL round-bottom flask equipped
  2. stirringto stir until gas evolution
  3. stirringto stir for 24 h
  4. customThe reaction was quenched by addition of a saturated aqueous solution of sodium bicarbonate (100 mL)
  5. washwashed with ethyl acetate (5×100 mL)
  6. washThe combined organic layers were washed with water (3×100 mL)
  7. customto remove dmf
  8. washfurther washed in brine (1×50 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe resulting yellow oil was purified by silica gel chromatography (96:4 hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-b57b7892b01d48ac82605be92960e8b5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552242B2

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