2-Methyl-2-butene → HCID 86680896, compound
Reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[S:40][C:41]([C:44]4[O:45][CH:46]=[CH:47][CH:48]=4)=[CH:42][N:43]=3)[CH:32]=2)[O:11][C@@H:10]1[CH:49]=[O:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.[OH:56]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+]>CC(O)(C)C.CC(O)=O>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[S:40][C:41]([C:44]4[O:45][CH:46]=[CH:47][CH:48]=4)=[CH:42][N:43]=3)[CH:32]=2)[O:11][C@@H:10]1[C:49]([OH:56])=[O:50])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
7
Procedure
To the solution of aldehyde 101 (830 mg, 1.17 mmol) in t-BuOH (34 mL) was added 2-methyl-2-butene (5.9 mL, 55.2 mmol), KH2PO4 (1.1 g, 8.3 mmol) and NaClO2 (960 mg, 10.6 mmol in H2O (20 mL)). The reaction mixture was stirred for 15 h at room temperature. The reaction mixture was acidified with AcOH and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide the desired acid 104 (815 mg, 96%) as a solid. The obtained acid was used without further purification. MH+722.
Workup
- extractionextracted with EtOAc
- dry with materialThe organic layer was dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c5edd37fbb3647038a90c193b4272236
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586550B2
Reaction notes
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