Cyclopentanone → HCID 69516114, compound

HRID 1297211Notes

Reaction equation

[H-].[Na+].[C:3]([N:22]1[N:26]=[N:25][C:24]([CH2:27][C:28]#[N:29])=[N:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:30]1(=O)[CH2:34][CH2:33][CH2:32][CH2:31]1>C1COCC1>[C:30]1(=[C:27]([C:24]2[N:25]=[N:26][N:22]([C:3]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:23]=2)[C:28]#[N:29])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a flask charged with dry sodium hydride (0.32 g, 13.3 mmol) was added (2-trityl-2H-tetrazol-5-yl)-acetonitrile (2.34 g, 6.67 mmol). The solids were swirled to mix, cooled to 0° C., and 25 mL THF was added quickly, resulting in vigorous H2 evolution and a bright yellow foam. The mixture was stirred at 0° C. for 5 min, at which time the ice bath was removed and stirring continued for 10 min. Cyclopentanone (0.65 mL, 7.33 mmol) in 10 mL THF was added quickly resulting in a clear orange solution. The mixture was stirred for 2 h, partitioned between EtOAc and sat. NH4Cl (aq), and the organic phase dried (MgSO4) and concentrated. Flash chromatography of the residue (CH2Cl2) furnished 2.05 g (74%) of cyclopentylidene-(2-trityl-2H-tetrazol-5-yl)-acetonitrile as a white solid. 1H NMR (CDCl3) δ 7.32 (m, 9H), 7.10 (m, 6H), 2.86 (m, 4H, —CH2CCH2—), 1.84 (m, 4H, —CH2CH2CH2CH2—).

Workup

additionto mix
customresulting in vigorous H2 evolution
customwas removed
customresulting in a clear orange solution
stirringThe mixture was stirred for 2 h
custompartitioned between EtOAc and sat. NH4Cl (aq)
dry with materialthe organic phase dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-42be4a27217d43569da0aae97de0855f
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250433B2

Reaction notes

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