Acetic Acid → 3beta-(Tert-butyldimethylsilyl)oxy-1alpha-(methoxymethyl)oxypregna-5,7-diene-20-carbaldehyde
Reaction equation
C(O)(=O)C.CC1(C)CO[CH:9]([CH:12]([C@@H:14]2[C@:31]3([CH3:32])[C@H:17]([C:18]4[C@H:28]([CH2:29][CH2:30]3)[C@:26]3([CH3:27])[C:21]([CH2:22][C@@H:23]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:24][C@@H:25]3[O:33][CH2:34][O:35][CH3:36])=[CH:20][CH:19]=4)[CH2:16][CH2:15]2)[CH3:13])[O:8]C1>O1CCCC1>[Si:38]([O:37][C@H:23]1[CH2:24][C@H:25]([O:33][CH2:34][O:35][CH3:36])[C@@:26]2([CH3:27])[C:21](=[CH:20][CH:19]=[C:18]3[C@@H:28]2[CH2:29][CH2:30][C@@:31]2([CH3:32])[C@H:17]3[CH2:16][CH2:15][C@@H:14]2[CH:12]([CH:9]=[O:8])[CH3:13])[CH2:22]1)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 5 ml of tetrahydrofuran was dissolved 20-(5,5-dimethyl-1,3-dioxan-2-yl)-3β-(tert-butyldimethylsilyl)oxy-1α-(methoxymethyl)oxypregna-5,7-diene, followed by addition of 5 ml of 80% acetic acid. The mixture was refluxed in an atmosphere of argon gas for 12 hours. The reaction mixture was then worked up in the same manner as Example 156 to give 50 mg of 3β-(tert-butyldimethylsilyl)oxy-1α-(methoxymethyl)oxypregna-5,7 -diene-20-carbaldehyde showing the following physical properties. 1H-NMR spectrum (90 MHz) δTMSCDCl 3: 0.13 (s, 6H), 0.66 (s, 3H), 0.95 (s, 9H), 1.01 (s, 3H), 1.14 (d, J=6.2 Hz, 3H), 3.40 (s, 3H), 4.10-4.50 (2H), 4.80 (br. s, 2H), 5.35 (m, 1H), 5.70 (m, 1H), 9.59 (d, J=3.5 Hz, 1H) IR spectrum (KBr): 1725 cm-1
Workup
- temperatureThe mixture was refluxed in an atmosphere of argon gas for 12 hours
Sources & evidence
- ORD record
- ord-fe4f2b4accef48d38e3a25f8eb3d128a
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05359055
Reaction notes
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