Triethylamine → HCID 86640981, compound
Reaction equation
[Br:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][OH:5].C(N(CC)CC)C.[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:15]([O:5][CH2:4][C:3]([CH3:7])([CH3:6])[CH2:2][Br:1])(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
3-Bromo-2,2-dimethyl-1-propanol (26.9 mL), 4-(dimethylamino)pyridine (2.67 g), and triethylamine (33.5 mL) were dissolved in toluene (250 mL) and cooled to 0° C. Pivaloyl chloride was added dropwise over 30 min (temperature rose to 15° C.) and upon completion the reaction was allowed to warm to 23° C. and stirred for 1 h. The reaction was filtered and the filtrate washed with 2N aqueous HCl (250 mL), aqueous sodium hydrogencarbonate solution (250 mL) and aqueous brine (250 mL). The organic layer was separated and the solvent evaporated to give the subtitle compound (53.0 g).
Workup
- temperatureto warm to 23° C.
- filtrationThe reaction was filtered
- washthe filtrate washed with 2N aqueous HCl (250 mL), aqueous sodium hydrogencarbonate solution (250 mL) and aqueous brine (250 mL)
- customThe organic layer was separated
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-1bc29b28cba24094a7efaa0123bf69fe
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012980B2
Reaction notes
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