Benzyl Alcohol → HCID 14213078, compound
Reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[C:20]([O:24][C:25]([CH2:27][C@@H:28]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:29](N1[C@H](C(C)C)COC1=O)=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21]>O1CCCC1>[CH2:1]([O:8][C:29](=[O:30])[C@H:28]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH2:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of dry benzyl alcohol (0.55 ml, 5.33 mmol) in anhydrous tetrahydrofuran (18 ml) under a nitrogen atmosphere at 0° C. was added a hexane solution of n-butyllithium (2.58 ml, 4.00 mmol). To this solution was added the product from Example 97 in anhydrous tetrahydrofuran (10 ml). After stirring 1 h at 0° C. the reaction was quenched by adding excess saturated aqueous ammonium chloride. The volatiles were removed by rotary evaporation and the resulting aqueous residue extracted two times with ether. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo provided an oil which was purified by chromatography on SiO2 (15% ether acetate/hexanes) to provide the desired product (0.89 g, 94%) as a colorless oil. Mass spectrum: (M)+ =354.
Workup
- customwas quenched
- additionby adding excess saturated aqueous ammonium chloride
- customThe volatiles were removed by rotary evaporation
- extractionthe resulting aqueous residue extracted two times with ether
- washThe combined organic layers were washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customprovided an oil which
- customwas purified by chromatography on SiO2 (15% ether acetate/hexanes)
Sources & evidence
- ORD record
- ord-50e129011a79417393c1a29a8cfee3d3
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05164388
Reaction notes
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