Ammonium Chloride → HCID 21949964, compound

HRID 2215756Notes

Reaction equation

[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[CH:20]([Mg]Br)=[CH2:21].[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:10]=1[NH:15][CH:21]=[CH:20]2)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of tert-butyl-dimethyl-[2-(2-nitro-phenyl)-ethoxy]-silane (5.0 g, 17.76 mmol) in THF (74 mL) was cooled to −65° C. and a 1.0 M solution of vinyl magnesium bromide in THF (53 mL, 53 mmol) was introduced while maintaining a temperature of <−40° C. The reaction was stirred for 15 minutes at −40° C., additional vinyl magnesium bromide (9 mL, 9 mmol) was added and the reaction was stirred at −45 to −40° C. for 25 minutes. The reaction was poured into saturated aq ammonium chloride and diluted with EtOAc (300 mL). The two layers were separated and the organic layer was dried (MgSO4), filtered and concentrated. Flash chromatography (95%hexane/EtOAc) gave the title compound (1.47 g, 30%) as a transparent oil. 1H NMR (400 MHz, DMSO-d6) −0.11 (s, 6H), 0.80 (s, 9H), 3.03 (t, J=6.8 Hz, 2H), 3.85 (t, J=6.8 Hz, 2H), 6.39 (dd, J=1.2, 3.2 Hz, 1H), 6.86–6.92 (m, 2H), 7.28 (dd, J=3, 3 Hz, 1H), 7.36 (dd, J=4.8, 4.8 Hz, 1H), 11.02 (br s, 1H). MS (electrospray, m/z) 276 (M++1).

Workup

temperaturewhile maintaining a temperature of <−40° C
stirringthe reaction was stirred at −45 to −40° C. for 25 minutes
customThe two layers were separated
dry with materialthe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-3093bca34a8e418abd4cc584404c2f4b
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109229B2

Reaction notes

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