Trimethylphosphine → HCID 22270570, compound

HRID 1160689Notes

Reaction equation

HRID 1160689 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:10][N:11]=[N+]=[N-])=[CH:4][CH:3]=1.CP(C)C.O.[OH-].[Li+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:10][NH2:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 68983TrimethylphosphineHCID 168937Lithium hydroxide, monohydrateHCID 85867954HCID 85867954, compound

Product 1

HCID 22270570HCID 22270570, compoundYield 203.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(4-chlorophenoylxy)-2-(4-chlorophenyl)ethyl azide (Step B, 0.23 g, 0.75 mmol) in 4 mLTHF at −20° C. was added trimethylphosphine (0.18 mL, 1.8 mmol), and the reaction was allowed to warm to room temperature over 2 h. Lithium hydroxide monohydrate (61 mg, 1.5 mmol) was added followed by 2 mL water. After stirring at room temperature for 30 min, the reaction was quenched by addition of 2 M hydrochloric acid (final pH=2). The volatile materials were removed on a rotary evaporator, and the resulting mixture was partitioned between brine (20 mL), 5 N aqueous sodium hydroxide (20 mL), ether (20 mL) and toluene (20 mL). The organic layer was separated and the aqueous layer extracted with ether (40 mL). The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated to dryness to give the title compound (0.43 g), which was contaminated with trimethylphosphine oxide and was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.46-7.40 (m, 4H), 7.20 (d, 2H), 6.91 (d, 2H), 5.53 (m, 2H), 3.36 (m, 2H). LC-MS: m/e 282 (M+H)+ (2.5 min).

Workup

  1. customthe reaction was quenched by addition of 2 M hydrochloric acid (final pH=2)
  2. customThe volatile materials were removed on a rotary evaporator
  3. customthe resulting mixture was partitioned between brine (20 mL), 5 N aqueous sodium hydroxide (20 mL), ether (20 mL) and toluene (20 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with ether (40 mL)
  6. dry with materialThe combined extracts were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1143705844724ae180fcf0d84fd37346
Source dataset
uspto-grants-2010_10
Patent number
US07816534B2

Reaction notes

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