3,4-dihydro-2H-pyran → 3-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile

HRID 585540Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

Conditions

Temperature: 25 °C

Procedure

3-(Hydroxymethyl)benzonitrile (5.00 g; 37.6 mmoles) and 3,4-Dihydro-2H-pyran (3.77 mL; 41.4 mmoles) were dissolved in methylene chloride (25 mL) under nitrogen and the solution was cooled to 5° C. p-Toluenesulfonic acid monohydrate (74 mg; 0.37 mmoles) was added and the mixture was stirred for 2 hours at 25° C. The reaction mixture was diluted with methylene chloride (25 mL). The solution was washed with aqueous sodium bicarbonate solution (30 mL) and aqueous sodium chloride solution (30 mL). The solution was dried over sodium sulfate and filtered. The solvent was removed under vacuum to give the product, 3-[(tetrahydro-2H-pyran-2-yloxy)methyl]benzo-nitrile (7.34 g; 89%) as an oil. 1H NMR (400 MHz) CDCl3 δ 7.68-7.70 (1H, m), 7.54-7.61 (2H, m), 7.42-7.48 (1H, m), 4.82 (1H, d, J=12.5 Hz), 4.72 (1H, t, J=3.3 Hz), 4.53 (1H, d, J=12.5 Hz), 3.84-3.92 (1H, m), 3.53-3.60 (1H, m), 1.60-1.95 (6H, m).

Workup

additionwas added
washThe solution was washed with aqueous sodium bicarbonate solution (30 mL) and aqueous sodium chloride solution (30 mL)
dry with materialThe solution was dried over sodium sulfate
filtrationfiltered
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-80f0936dc0c4428bb6b8142a668723df
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933304B2

Reaction notes

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