Diethyl Ether → HCID 20675217, compound

HRID 1387607Notes

Reaction equation

Cl.[C:2]1([P:8]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)C.CC(C)([O-])C.[K+]>C(Cl)Cl>[C:2]1([P:8]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([NH:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3 (3.00 g, 6.94 mmol) in 100 mL dry CH2Cl2 was placed in a 500 mL Schlenk flask under N2 and cooled to 0° C. in an ice bath. A diethyl ether solution of potassium t-butoxide (0.79 g, 7.0 mmol) was added to the flask by cannula. The reaction mixture was stirred for 5 minutes and the volatiles were removed under vacuum. The remaining solid was extracted with toluene. Removal of toluene from the extract afforded a white solid which was further purified by recrystallization from toluene and hexane. Yield: 2.2 g (5.6 mmol, 81%). 1H NMR (CDCl3): δ 7.9-7.2 (20H, aromatic protons), 4.22 (d, 4H, NCH2Ph, 3JPH=14.0 Hz); 13C{1H} NMR (CDCl3): δ 132.2, 132.0, 131.2, 128.6, 127.5, 126.4 (aromatic carbons), 46.1 (NCH2Ph); 31P{1H} NMR (CDCl3): 8 14.2. Analysis calculated for C26H25PN2: C, 78.77; H, 6.36; N, 7.07. Found: C, 79.00; H, 6.37; N, 6.86.

Workup

customthe volatiles were removed under vacuum
extractionThe remaining solid was extracted with toluene
customRemoval of toluene from the extract
customafforded a white solid which
customwas further purified by recrystallization from toluene and hexane

Sources & evidence

ORD record: ord-42a1b87002c943518ae0aaf901c56a4f
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268448B1

Reaction notes

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