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

HRID 840327

反応式

HRID 840327 の反応式
[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]

参加物

4

反応物 2

HCID 9550DiazomethaneHCID 94391Dehydroabietic Acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0d57aebf73bb4dee894d4744096feef7
出典データセット
uspto-grants-2002_04
特許番号
US06365634B1

関連ノート

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