Pyridine → 7-Methyl-14,15-methyleneestr-4-en-3-one

HRID 49414ノート

反応式

HRID 49414 の反応式
OC[C@@H:3]1[CH2:8][C@H:7]2[CH2:9][C@@:6]32[C@H:10]2[C@H:19]([CH2:20][CH2:21][C@:4]13[CH3:5])[C@@H:18]1[C:13](=[CH:14][C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][C@H:11]2[CH3:23].N1C=CC=CC=1.C(OC(=O)C)(=O)C>O1CCCC1>[CH3:23][CH:11]1[CH2:12][C:13]2[C@H:18]([CH2:17][CH2:16][C:15](=[O:22])[CH:14]=2)[C@@H:19]2[C@@H:10]1[C@:6]13[CH2:9][CH:7]1[CH2:8][CH2:3][C@:4]3([CH2:21][CH2:20]2)[CH3:5]

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 9796915(7alpha,14beta,15beta,17alpha)-17-(Hydroxymethyl)-7-methyl-14,15-methyleneestr-4-en-3-one

生成物 1

HCID 701471477-Methyl-14,15-methyleneestr-4-en-3-one収率 121.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (7α,14β,15β,17α)-17-(hydroxymethyl)-7-methyl-14,15-methyleneestr-4-en-3-one (Example 1, 0.20 g) in a mixture of dry pyridine (1.76 ml) and dry tetrahydrofuran (8.8 ml) was treated with acetic anhydride (1.06 ml). The mixture was stirred at room temperature overnight and then quenched with water. After 1 h stirring the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (7α,14β,15β,17α)17-[(acetyloxy)methyl)]-7-methyl-14,15-methyleneestr-4-en-3-one (0.22 g). 1H NMR (CDCl3) δ5.80 (t, 1H, J=2.8 Hz), 4.05 (dd, part A of AB system, 1H, J=11.0 and 6.3 Hz), 3.95 (dd, part B of AB system, 1H, J=11.0 and 7.1 Hz), 2.03 (s, 3H), 1.08 (s, 3H),. 0.62 (d, 3H, J=7.1 Hz), 0.48 (dd, 1H, J=8.3 and 5.1 Hz), 0.27 (dd, 1H, J=5.1 and 3.5 Hz).

後処理

  1. customquenched with water
  2. stirringAfter 1 h stirring the product
  3. extractionwas extracted into ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6067c95a42754a5ab37fe2b3f10db854
出典データセット
uspto-grants-2004_03
特許番号
US06706700B2

反応ノート

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