Hydrochloric Acid → HCID 66692279, compound
Reaction equation
[Li+].CC([N-]C(C)C)C.[CH2:9]1[CH2:14]CC[CH2:11][CH2:10]1.[OH:15][C:16]1[CH:21]=[C:20]([CH3:22])[O:19][C:18](=[O:23])[C:17]=1[C:24](=[O:33])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.ICCCC.CN(P(N(C)C)(N(C)C)=O)C.Cl>C1COCC1>[OH:15][C:16]1[CH:21]=[C:20]([CH2:22][CH2:14][CH2:9][CH2:10][CH3:11])[O:19][C:18](=[O:23])[C:17]=1[C:24](=[O:33])[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
1.5 M LDA in cyclohexane (1.34 ml; 2 mmol; Aldrich) was added to 4-hydroxy-6-methyl-3-(3-phenylpropanoyl)-2-pyrone (258.27 mg; 1 mmol; Example 1.1) in 8.4 ml anhydrous THF, and the reaction mixture was stirred under N2 for 0.5 h at 0° C. 1-iodo-butane (136.8 μl; 1.2 mmol; Aldrich) and HMPA (167 ul; 0.96 mmol: Aldrich) were added sequentially under N2, and the reaction mixture was stirred under N2 for 2 h at 0° C. and 5 h at room temperature. The reaction mixture was acidified by addition of 1 N HCl (16 ml) and extracted with ethyl acetate (3×20 ml). The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. The product was isolated by chromatography on silica gel. Yield: 20%. MS (MALDI): calculated, m/z 315.2 (MH+); found, 315.1.
Workup
- stirringthe reaction mixture was stirred under N2 for 2 h at 0° C. and 5 h at room temperature
- extractionextracted with ethyl acetate (3×20 ml)
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous Na2SO4
- customevaporated under vacuum
- customThe product was isolated by chromatography on silica gel
Sources & evidence
- ORD record
- ord-30b80e70e139417ab1d9327b72b60536
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772332B2
Reaction notes
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