trans-6-Shogaol → Paradol

HRID 918998

반응식

HRID 918998 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[C:8]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=1)=[O:9]>C1COCC1.[Pd]>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[CH:13][C:14]=1[O:19][CH3:20]

참가 물질

4

반응물 1

HCID 5281794trans-6-Shogaol

생성물 1

HCID 94378Paradol

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of [6]-shogaol (276 mg, 1.0 mmol) in THF (2 mL) at rt was treated with 10% Pd/C (30 mg, 10% w/w) under H2. The mixture was stirred at rt overnight and filtered. The filtrate was concentrated under reduced pressure. The residue was loaded to preparative TLC (hexane/EtOAc=8:1) to give the title compound M11 as a yellow oil (272 mg, yield 98%); 1H NMR (600 MHz, CDCl3) δ 6.69 (1H, d, J=1.6 Hz, H-2′), 6.82 (1H, d, J=8.0 Hz, H-5′), 6.66 (1H, dd, J=8.0, 1.7 Hz, H-6′), 2.69 (2H, t, J=7.4 Hz, H-1), 2.82 (2H, t, J 7.4 Hz, H-2), 2.37 (1H, t, J=7.4 Hz, H-4), 1.54 (2H, m, H-5), 1.30-1.24 (8H, m, ranged from H-6 to H-9), 0.87 (3H, t, J=6.8 Hz, H-10), and 3.87 (3H, s, OMe-3′); positive APCIMS, m/z 279 [M+H]+.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-54e4a481a6d64edfa2830da014d36c0b
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09272994B1

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