Pyridine → 7-Methyl-14,15-methyleneestr-4-en-3-one
Reaction equation
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]Participants
Procedure
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).
Workup
- customquenched with water
- stirringAfter 1 h stirring the product
- extractionwas extracted into ethyl acetate
- washThe combined organic phases were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6067c95a42754a5ab37fe2b3f10db854
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706700B2
Reaction notes
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