Hydrochloric Acid → HCID 20533589, compound
Reaction equation
[Mg].C(Br)C.CC#C.[O:8]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1C=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[O:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[C:26]([CH:25]([OH:24])[C:21]1[CH:20]=[CH:19][CH:16]=[C:15]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:22]=1)#[C:27][CH3:28]Participants
Procedure
A Grignard solution, freshly prepared from 4 g of magnesium and 20 g of ethyl bromide in 20 ml of tetrahydrofuran, is slowly added at 0° C. to a solution of 8 g of methylacetylene in 100 ml of tetrahydrofuran, and the mixture is stirred under argon for 15 minutes. There is then added dropwise to this mixture at 0° to 5° C. a solution of 27 g of o-phenoxybenzaldehyde in 100 ml of tetrahydrofuran. After being stirred for 14 hours at room temperature, the reaction mixture is cooled to 0° C. with 50 g of ice; 25 ml of conc. hydrochloric acid is subsequently slowly added, and extraction is performed with ether. The ether extract is washed twice with water and twice with saturated sodium chloride solution; it is then dried over sodium sulfate, filtered, and concentrated by evaporation. The product is chromatographed through silica gel with ethyl acetate/hexane (1:1) as the eluant. There is thus obtained the compound of the formula ##STR5## having a refractive index of nD20 =1.5898.
Workup
- stirringAfter being stirred for 14 hours at room temperature
- extractionextraction
- extractionThe ether extract
- washis washed twice with water and twice with saturated sodium chloride solution
- dry with materialit is then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated by evaporation
- customThe product is chromatographed through silica gel with ethyl acetate/hexane (1:1) as the eluant
- customThere is thus obtained the compound of the formula
Sources & evidence
- ORD record
- ord-1b03df2bdacc46439e7391725bea13a1
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04782087
Reaction notes
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