Water → HCID 14069397, compound

HRID 910712Notes

Reaction equation

[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15]O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[I-].[C:18]([CH2:20][P+](C)(C)C)#[N:19].C(N(C(C)C)CC)(C)C.O>C(#N)CC>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][CH2:20][C:18]#[N:19])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 97 °C

Procedure

To a solution of anthracen-9-yl-methanol (6.58 g, 31.6 mmol) and (cyanomethyl)trimethylphosphonium iodide (19.19 g, 78.96 mmol) in propionitrile (77 mL) was added diisopropylethylamine (DIPEA, 49.4 mL, 94.74 mmol) and the mixture was stirred at 97° C. for 20 hours. Water (3.82 mL) was added, nitrogen was bubbled though the mixture, and the mixture was stirred for 20 hours. Water (480 mL) and concentrated HCl (19 mL) were added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated. The resulting solid was purified by silica gel column chromatography (hexane:CHCl3=1:1) to give 3-anthracen-9-yl-propionitrile as brown crystals (6.93 g, 95% yield). 1H NMR (CDCl3) δ 8.43 (1H, s), 8.19 (2H, d), 8.05 (2H, d), 7.60 (2H, dd), 7.51 (2H, dd), 4.02 (2H, t), 2.79 (2H, t).

Workup

customnitrogen was bubbled though the mixture
stirringthe mixture was stirred for 20 hours
additionWater (480 mL) and concentrated HCl (19 mL) were added
extractionthe mixture was extracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe resulting solid was purified by silica gel column chromatography (hexane:CHCl3=1:1)

Sources & evidence

ORD record: ord-1f18fe9c274846f4bdb439148a936788
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022214B2

Reaction notes

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