Reaction equation
[OH-:1].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1CC#N.Br[CH2:17][CH2:18]Cl.[CH2:20]([OH:23])[CH2:21]O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:8]=[CH:9][C:10]=1[C:21]1([C:20]([OH:23])=[O:1])[CH2:18][CH2:17]1Participants
Conditions
- Temperature
- 100 °C
Procedure
Sodium hydroxide (50% aqueous solution, 3.20 g, 0.0552 mol) was added to a mixture of 2-naphthylacetonitrile (0.913 g, 0.00546 mol), benzyltriethylammonium chloride (0.09 g, 0.0004 mol), and 1-bromo-2-chloro-ethane (1.58 g, 0.0110 mol) at 50 celsius for 5 h. Then 1,2-ethanediol (10.0 mL, 0.179 mol) was added and the mixture was heated at 100° C. overnight. The mixture was poured into ice-water (30 mL) and was extracted with ethyl ether (2×10 mL). The aqueous phase was acidified (pH=2) with 1N HCl and was extracted with ethyl acetate (4×15 mL). The combined organic phase was washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was the desired product, which was directly used in next step reaction without further purification.
Workup
- extractionwas extracted with ethyl ether (2×10 mL)
- extractionwas extracted with ethyl acetate (4×15 mL)
- washThe combined organic phase was washed with brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customwas directly used in next step reaction without further purification
Sources & evidence
- ORD record
- ord-b0770cc97ca6438b91ff5aa7f4ba3328
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776874B2
Linked notes
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