Phosphorus oxychloride → HCID 91619162, compound
Reaction equation
[CH:1]([NH:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:6][CH:5]=1)=O.O=P(Cl)(Cl)Cl>C1COCC1>[N+:3]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])=[CH:6][CH:5]=1)#[C-:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To Intermediate 1A in THF (300 mL) was added TEA (33 mL, 238 mmol) and, after cooling to 0° C., POCl3 (7.3 mL, 79 mmol) was slowly added and the reaction was stirred at room temperature. After 24 h, the reaction was partitioned between EtOAc (200 mL) and aqueous NaHCO3 (100 mL). The aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed with brine (50 mL) and dried (MgSO4). Purification by normal phase chromatography afforded 10.4 g (64.6%) of Intermediate 1 as a green solid. 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=8.59 Hz, 2H), 7.41 (d, J=8.34 Hz, 2H), 1.60 (s, 9H) ppm.
Workup
- customthe reaction was partitioned between EtOAc (200 mL) and aqueous NaHCO3 (100 mL)
- extractionThe aqueous layer was extracted with EtOAc (100 mL)
- washThe combined organic layers were washed with brine (50 mL)
- dry with materialdried (MgSO4)
- customPurification by normal phase chromatography
Sources & evidence
- ORD record
- ord-982b1455f7764c67943f4f756743c06b
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315519B2
Reaction notes
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