Pyridine → (R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester
Reaction equation
[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Br:19][CH2:20][C:21](Br)=[O:22].N1C=CC=CC=1>>[CH3:7][O:6][C:4](=[O:5])[CH2:3][C@H:2]([O:1][C:21](=[O:22])[CH2:20][Br:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]Participants
4
Procedure
To a rapidly-stirred slurry of 1.29 g (4.99 mmol) methyl (R)-3-hydroxytetradecanoate and 0.45 mL (5.2 mmol) bromoacetyl bromide in 25 mL hexanes at 0° C. in a flame-dried flask under N2 was added 0.42 mL (5.2 mmol)pyridine all at once. The mixture was removed from the cold bath for 30 min. The mixture was suction filtered through celite, washing with 75 mL ether. The filtrate was washed with 2×100 mL H2O and with 50 mL 10% NaHCO3. The ether was dried over MgSO4 and removed by rotary evaporation, giving 1.70 g (90%) crude (R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester as a yellow oil. Analytically pure samples could be prepared by subjecting the oil to radial chromatography, eluting with CH2Cl2.
Workup
- customThe mixture was removed from the cold bath for 30 min
- filtrationfiltered through celite
- washwashing with 75 mL ether
- washThe filtrate was washed with 2×100 mL H2O and with 50 mL 10% NaHCO3
- dry with materialThe ether was dried over MgSO4
- customremoved by rotary evaporation
Sources & evidence
- ORD record
- ord-7c2f73a24f63430ba9a8bba96e3cd535
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05274143
Reaction notes
Loading…