Hydrochloric Acid → HCID 57710196, compound
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Mg].[O:11]1[CH2:15][CH2:14][NH:13]C1.Cl.[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>C1(C)C=CC=CC=1.II>[OH:11][CH2:15][CH2:14][N:13]1[CH2:17][CH2:21][O:20][CH2:19][CH:18]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
25 g of 1-Bromooctane were slowly added to a suspension of 3.5 g of magnesium and 7.5 mg of iodine in 41 ml of THF at 65° C. The reaction mixture was stirred at the same temperature for 2 h. When the corresponding Grignard compound was prepared, the mixture was cooled down at 5° C. and a solution of 16.7 g of Oxazolidine (II) in 40 ml of toluene was added in 1 hour. The mixture was stirred at 5° C. for 30 min. and the reaction was warmed up until room temperature. The mixture was added to an aqueous solution of 5% HCl and stirred for 30 min. The organic layer was decanted, dried and concentrated until dryness to obtain 19 g of the desired compound as a brown oil. MS (EI), (m/z, %): 243 (M+., 5), 242 (M-H, 5), 212 (M-CH2OH, 50), 198 (M-(CH2)2OH, 8), 130 (M-C8H17, 100), 112 (M-C8H17-H2O, 8), 100 (M-73, 30), 86 (8), 71 (8), 56(9), 41 (14).
Workup
- customWhen the corresponding Grignard compound was prepared
- stirringThe mixture was stirred at 5° C. for 30 min.
- temperaturethe reaction was warmed up until room temperature
- stirringstirred for 30 min
- customThe organic layer was decanted
- customdried
- concentrationconcentrated until dryness
Sources & evidence
- ORD record
- ord-3b75c66d926c43f6acfddd999c834413
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143463B2
Reaction notes
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