(4-Cyanonaphthalen-1-yl)acetic acid → 4-(2-Hydroxyethyl)-1-naphthonitrile
Reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][C:14](O)=[O:15])=[CH:5][CH:4]=1)#[N:2]>C1COCC1>[OH:15][CH2:14][CH2:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of (4-cyanonaphthalen-1-yl)acetic acid (100 mg, 0.47 mmol) in THF (6 mL) was treated with borane dimethyl sulfide complex (2M, 0.47 mL, 0.94 mmol) and the reaction was stirred for 3 hours at room temperature. The reaction was quenched with methanol and the mixture was partitioned with ethyl acetate and 2N HCl/water. The aqueous was extracted again with ethyl acetate and the organic layers were washed with brine, dried over sodium sulfate and evaporated. The residue was purified on a CombiFlash Rf (12 gm, gradient 10-80% ethyl acetate in hexanes) to afford the title alcohol as an oil. 1H-NMR (500 MHz, CDCl3) δ ppm 1.80 (br s, 1H), 3.48 (t, J=6.4 Hz, 2H), 4.10 (t, J=6.4 Hz, 2H), 7.52 (d, J=7.3 Hz, 1H), 7.75 (m, 2H), 7.92 (d, J=7.2 Hz, 1H), 8.22 (d, J=8.2 Hz, 1H). 8.34 (d, J=8.0 Hz, 1H).
Workup
- additionwas treated with borane dimethyl sulfide complex (2M, 0.47 mL, 0.94 mmol)
- customThe reaction was quenched with methanol
- customthe mixture was partitioned with ethyl acetate and 2N HCl/water
- extractionThe aqueous was extracted again with ethyl acetate
- washthe organic layers were washed with brine
- dry with materialdried over sodium sulfate
- customevaporated
- customThe residue was purified on a CombiFlash Rf (12 gm, gradient 10-80% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-34cfc445906a491393887657706d4473
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073882B2
Reaction notes
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