Acetyl ferulate → HCID 178445892, compound
Reaction equation
[CH3:1][C@@H:2]([C@@H:10]1[C@@:14]2([CH3:31])[CH2:15][CH2:16][C@@:17]34[CH2:23][C@:22]53[CH2:24][CH2:25][C@H:26]([OH:30])[C:27]([CH3:29])([CH3:28])[C@@H:21]5[CH2:20][CH2:19][C@H:18]4[C@:13]2([CH3:32])[CH2:12][CH2:11]1)[CH2:3][CH2:4][C:5]([CH:7]([CH3:9])[CH3:8])=[CH2:6].C([O:36][C:37]1[CH:47]=[CH:46][C:40]([CH:41]=[CH:42][C:43]([O-:45])=[O:44])=[CH:39][C:38]=1[O:48][CH3:49])(=O)C.C(OC(=O)C)(=O)/C=C/C1C=CC(O)=C(OC)C=1>>[CH3:1][C@@H:2]([C@@H:10]1[C@@:14]2([CH3:31])[CH2:15][CH2:16][C@@:17]34[CH2:23][C@:22]53[CH2:24][CH2:25][C@H:26]([OH:30])[C:27]([CH3:29])([CH3:28])[C@@H:21]5[CH2:20][CH2:19][C@H:18]4[C@:13]2([CH3:32])[CH2:12][CH2:11]1)[CH2:3][CH2:4][C:5]([CH:7]([CH3:8])[CH3:9])=[CH2:6].[OH:36][C:37]1[CH:47]=[CH:46][C:40]([CH:41]=[CH:42][C:43]([O-:45])=[O:44])=[CH:39][C:38]=1[O:48][CH3:49]Participants
Procedure
Commercial available γ-oryzanol (100 g, 24-methylenecycloartanol content 45%) was acetylated with acetic anhydride in pyridine. This acetylated γ-oryzanol was recrystallized repeatedly from chloroform-ethyl acetate-ethanol (4:3:2, V/V), giving acetyl ferulate (18 g) of 24-methylenecycloartanol content 95%. This acetyl ferulate was completely saponified in the solution of 2N NaOH-ethanol, then the obtained alcohol was converted into the benzoate. This benzoate was recrystallized repeatedly, and completely saponified to give 24-methylenecycloartanol (5 g). A portion (2 g, 0.0045 mole) thereof wa converted into 24-methylenecycloartanol-4-acetoxy-3-methoxycinnamate according to following the procedure of Example 65. This ester was then deacetylated according to following the procedure of Example 100-2, giving 24-methylenecycloartanol-4-hydroxy-3-methoxycinnamate (2.58 g), in a 90% yield. m.p. 166°-167° C.
Sources & evidence
- ORD record
- ord-fb90e096c2004123995b43592da3dd37
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04748161
Reaction notes
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