Hexane → HCID 86044196, compound
Reaction equation
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].C([Li])CCC.CCCCCC.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]C>C1COCC1.C(O)C>[CH2:10]([O:9][C:3](=[O:8])[CH2:4][C:5](=[O:6])[CH2:7][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24])[CH3:11]Participants
Procedure
To a solution of sodium hydride (1.2 g, 50 mmol) in THF, distilled ethyl acetoacetate (4.16 g, 32 mmol) was added dropwise. The resulting mixture was stirred for 30 min at room temperature and then cooled at −78° C. A solution of n-butyllithium in hexane (16.1 mL, 35.2 mmol) was added dropwise. After stirring for an additional 1 h at 0° C., 1-bromohexadecane (19.1 mmol) in THF was added and the mixture was stirred for 12 h. Ethanol (15 mL) was added slowly at room temperature. The resulting solution was filtered through a Celite pad, concentrated in vaccum and purified by chromatography on silica gel to give the 3-oxo-nonadecanoic acid ethyl ester as a solid. Anal. C21H40O3: Calcd: C, 74.07; H, 11.84; O, 14.09. Found: C, 73.98; H, 11.59; O, 14.25. MS (ESIMS): m/z: 340.3.
Workup
- additionwas added dropwise
- temperaturecooled at −78° C
- stirringAfter stirring for an additional 1 h at 0° C.
- stirringthe mixture was stirred for 12 h
- filtrationThe resulting solution was filtered through a Celite pad
- concentrationconcentrated in vaccum
- custompurified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-4e0ddd37fc614333ac4c6fc40782bf6e
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812251B2
Reaction notes
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