Pyridine → Tricyclo(3.3.1.13,7)decane-1-carboxylic acid, (3-phenoxyphenyl)methyl
Reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[O:14]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][OH:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1>C1C=CC=CC=1>[C:1]12([C:11]([O:25][CH2:24][C:23]3[CH:26]=[CH:27][CH:28]=[C:21]([O:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:22]=3)=[O:12])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1 g (5.03 mmol) of tricyclo[3.3.1.13,7 ]decane-1-carbonyl chloride, 1.01 g (5.04 mmol) of 3-phenoxybenzyl alcohol and 0.08 g (10.07 mmol) of anhydrous pyridine were dissolved in 30 ml of anhydrous benzene. The mixture was stirred at room temperature for 66 hours. Then the reaction was terminated. The resulting pyridine hydrochloride was removed by filtration and the filtrate was thoroughly washed with 1N hydrochloric acid, 5% sodium carbonate and then saturated saline solution, and dried over sodium sulfate. The solvent was removed to obtain 1.8 g of an oily material. Purification by column chromatography on silica gel employing a developer consisting of n-hexane and benzene (1:1) gave 1.69 g (yield 93%) of a colorless oily material.
Workup
- customThen the reaction was terminated
- customThe resulting pyridine hydrochloride was removed by filtration
- washthe filtrate was thoroughly washed with 1N hydrochloric acid, 5% sodium carbonate
- dry with materialsaturated saline solution, and dried over sodium sulfate
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-cd3cfd4fb4ff45c3a5b930badd7a7106
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04529599
Reaction notes
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