Diazomethane → Methyl abieta-8,11,13-trien-18-oate

HRID 840327

반응식

HRID 840327 반응식
[CH3:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]2[C@@:13]3([CH3:22])[CH2:14][CH2:15][CH2:16][C@:17]([C:19]([OH:21])=[O:20])([CH3:18])[C@@H:12]3[CH2:11][CH2:10][C:8]=2[CH:9]=1)[CH3:3].[N+](=[CH2:25])=[N-]>CO>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]2[C:13]3([CH3:22])[CH:12]([CH2:11][CH2:10][C:8]=2[CH:9]=1)[C:17]([C:19]([O:21][CH3:25])=[O:20])([CH3:18])[CH2:16][CH2:15][CH2:14]3)[CH3:1]

참가 물질

4

반응물 2

HCID 9550DiazomethaneHCID 94391Dehydroabietic Acid

생성물 1

HCID 247581Methyl abieta-8,11,13-trien-18-oate수율 82,242.297%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

Dehydroabietic acid (50 mg, 0.116 μmol, Helix Biotech) was dissolved in 2 ml of methanol (HPLC grade, Fisher Scientific) and cooled to 0° C. on ice in a round bottom flask. An excess (30 μmol) of ethereal diazomethane (obtained by distillation) was added and the reaction was stirred for 5 minutes. The non-reacted diazomethane was evaporated and solvent was then removed by rotary evaporation. This reaction is shown schematically in FIG. 4. The product was purified by preparative TLC (1000 μm PK6F 60 Å, Whatman) silica gel plates developed in hexane:ethyl acetate 95:5 (v:v, Rf: 0.25). This step provided 30 mg of a clear oil as the methyl ester that was pure by NMR (see FIG. 5). 1H NMR (CDCl3, 300 MHz) δ1.35-1.42 (m, 12H), 1.50-2.05 (m, 7H), 2.43 (t, J=8.80 Hz, 2H), 2.90-3.05 (m, 3H), 3.80 (s, 3H), 7.02 (s, 1H), 7.14 (d, J=8.19 Hz, 1H), 7.31 (d, J=8.19 Hz, 1H). The product also gave the following electron impact mass spectra: (%) 315 (2.9, M+1), 314 (13, M), 299 (16.4), 240 (20.1), 239 (100), 197 (6.1), 173 (5.0), 141 (5.7).

후처리

  1. customThe non-reacted diazomethane was evaporated
  2. customsolvent was then removed by rotary evaporation
  3. customThe product was purified by preparative TLC (1000 μm PK6F 60 Å, Whatman) silica gel plates

출처 및 근거

ORD 기록
ord-0d57aebf73bb4dee894d4744096feef7
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365634B1

연결된 노트

불러오는 중…