Phosphorus oxychloride → HCID 91619162, compound

HRID 1477106Notes

Reaction equation

HRID 1477106 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

HCID 24813Phosphorus oxychlorideHCID 22291289HCID 22291289, compound

Product 1

HCID 91619162HCID 91619162, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To Intermediate 1A in THF (300 mL) was added TEA (33 mL, 238 mmol) and the 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

  1. customthe reaction was partitioned between EtOAc (200 mL) and aqueous NaHCO3 (100 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (100 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-07a8a3ed48b34db2b3cde5a8678b6459
Source dataset
uspto-grants-2016_08
Patent number
US09403774B2

Reaction notes

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