Pyridine → HCID 21711993, compound
Reaction equation
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][O:27][C:28](=[O:45])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][OH:44])=[O:24].N1C=CC=CC=1>C(Cl)Cl>[Cl:6][CH2:5][O:4][C:2]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][O:27][C:28](=[O:45])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:44][C:2]([O:4][CH2:5][Cl:6])=[O:3])=[O:24])=[O:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Chloromethyl chloroformate (0.93 g, 7.2 mmol) was added to an ice-cooled solution of methylene bis(16-hydroxyhexadecanoate) (2.0 g, 3.6 mmol) in methylene chloride (80 ml). Pyridine (0.57 g, 7.2 mmol) was added and the reaction mixture was stirred for 15 minutes at 0° C. and 4 hours at room temperature The reaction mixture was washed with hydrochloric acid (1M, 50 ml) saturated aqueous sodium bicarbonate (50 ml), water (50 ml) and dried (MgSO4). The solvent was evaporated and the residue was purified by flash chromatography (silica/methylene chloride). Yield: 84% 1H NMR (200 MHz, CDCl3): δ 1.25 (m, 44H), 1.72 (m, 8H), 2.31 (t, 4H), 4.20 (t, 4H), 5.72 (m, 6H).
Workup
- washwas washed with hydrochloric acid (1M, 50 ml) saturated aqueous sodium bicarbonate (50 ml), water (50 ml)
- dry with materialdried (MgSO4)
- customThe solvent was evaporated
- customthe residue was purified by flash chromatography (silica/methylene chloride)
Sources & evidence
- ORD record
- ord-5dc25ef172524d1fac23e15544d41d22
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06274120B1
Reaction notes
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