Ethanol → HCID 20695145, compound

HRID 1803036Notes

Reaction equation

[C:1]1([P:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23](O)[CH3:24].C(N=C=NC(C)C)(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]1([P:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([O:12][CH2:23][CH3:24])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(Diphenylphosphanyl)benzoic acid (0.50 g, 1.63 mmol) and 4-dimethylaminopyridine (DMAP, 20 mg, 0.163 mmol) were dissolved in CH2Cl2 (10 mL). Ethanol (0.29 mL, 4.89 mmol) was added, and the solution was placed under Ar(g) and cooled to 0° C. N,N′-Diisopropylcarbodiimide (DIC, 0.25 mL, 1.63 mmol) was added dropwise, and the resulting solution was allowed to warm to room temperature and stirred overnight. The solution was then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography, eluting with 10% EtOAc(ethylacetate)/hexanes, to give phosphine 1a as a pale yellow solid (0.44 g, 1.32 mmol, 81% yield). 2-(Diphenylphosphanyl)benzoic acid was purchased from Sigma-Aldrich (St. Louis, Mo.).

Workup

temperatureto warm to room temperature
filtrationThe solution was then filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography
washeluting with 10% EtOAc(ethylacetate)/hexanes

Sources & evidence

ORD record: ord-cf2379a2b8b642f9ab219819c88b88b9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08350014B2

Reaction notes

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