5-Fluoro-2-nitrobenzaldehyde → HCID 68978639, compound

HRID 658061Notes

Reaction equation

C(OP([CH:9]([C:17]#[N:18])[CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)(=O)OCC)C.[F:19][C:20]1[CH:21]=[CH:22][C:23]([N+:28]([O-:30])=[O:29])=[C:24]([CH:27]=1)[CH:25]=O>C1COCC1.C(OCC)(=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([N+:28]([O-:30])=[O:29])=[C:24]([CH:25]=[C:9]([CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:17]#[N:18])[CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

[1-Cyano-2-(tetrahydro-pyran-4-yl)-ethyl]-phosphonic acid diethyl ester (5.4 g, 19.6 mmol) was dissolved in THF (100 mL) and cooled to 0° C. Lithium (bistrimethylsilyl)amide (20 mL, 20 mmol, [1M]) was the added dropwise. The resulting mixture was stirred 20 min, and then 5-fluoro-2-nitro-benzaldehyde (3.31 g, 19.6 mmol) was added. The resulting mixture was stirred at room temperature overnight, then diluted with ethyl acetate and washed with saturated aqueous NaHCO3 solution. The organic phase was separated and dried with MgSO4 and filtered. The solvent was removed to yield an oil which was purified by silica column chromatography (120 g column, 20% EtOAc/heptane) to yield a solid.

Workup

additionadded dropwise
stirringThe resulting mixture was stirred at room temperature overnight
washwashed with saturated aqueous NaHCO3 solution
customThe organic phase was separated
dry with materialdried with MgSO4
filtrationfiltered
customThe solvent was removed
customto yield an oil which
customwas purified by silica column chromatography (120 g column, 20% EtOAc/heptane)
customto yield a solid

Sources & evidence

ORD record: ord-3502708835bf46edbbd2460ba8ddbfbb
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076358B2

Reaction notes

Loading…