Ammonium Chloride → HCID 11071548, compound

HRID 975488Notes

Reaction equation

[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([NH:17][CH:18]([P:20]([CH:25](Br)[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(=[O:24])[O:21][CH2:22][CH3:23])Br)=[O:16])([CH3:13])([CH3:12])[CH3:11].[Cl-].[NH4+]>C1COCC1>[C:10]([O:14][C:15]([NH:17][CH:18]([P:20]([CH:25]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:24])[O:21][CH2:22][CH3:23])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

A 2.00N benzylmagnesium chloride solution (1.35 ml; 2.70 mmol) in THF is added dropwise to a solution of the bromide 6 (340 mg; 0.67 mmol) in THF (10 ml), which is stirred at -78° C. under an argon atmosphere. After stirring at -70° C. for 3 hours, the reaction solution is warmed to room temperature and mixed with saturated aqueous ammonium chloride solution (50 ml). The aqueous phase is extracted with ethyl acetate (3×60 ml). The combined organic phase is dried over Na2SO4 and concentrated under reduced pressure. After purification by column chromatography on silica gel (ethyl acetate/heptane), the bisalkylated phosphinic acid ester 10 (105 mg, 30% of theory) is obtained.

Workup

stirringAfter stirring at -70° C. for 3 hours
temperaturethe reaction solution is warmed to room temperature
extractionThe aqueous phase is extracted with ethyl acetate (3×60 ml)
dry with materialThe combined organic phase is dried over Na2SO4
concentrationconcentrated under reduced pressure
customAfter purification by column chromatography on silica gel (ethyl acetate/heptane)

Sources & evidence

ORD record: ord-0adf3cbfb77c43d98f5b3fa66e144c65
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608098

Reaction notes

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