Acetonitrile → HCID 67317029, compound

HRID 875514Notes

Reaction equation

HRID 875514 reaction equation
[CH:1]1([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:16](#[N:18])[CH3:17]>>[CH:1]1([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:11]([OH:12])[CH2:17][C:16]#[N:18])[CH:13]=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 54026880HCID 54026880, compound

Product 1

HCID 67317029HCID 67317029, compound

Procedure

Aldol condensation with acetonitrile and 3-(cyclopentylmethoxy)benzaldehyde gave 3-(3-(cyclopentylmethoxy)phenyl)-3-hydroxypropanenitrile as a colorless oil. Yield (0.4 g, 38%): 1H NMR (400 MHz, CDCl3) δ 7.22-7.28 (m, 1H), 6.88-6.94 (m, 2H), 6.82-6.88 (m, 1H), 4.95 (t, J=6.4 Hz, 1H), 3.81 (d, J=6.4 Hz, 2H), 2.83 (brs, 1H), 2.71 (d, J=6.4 Hz, 2H), 2.33 (dddd, J=7.2 Hz, 1H), 1.76-1.88 (m, 2H), 1.50-1.68 (m, 4H), 1.28-1.40 (m, 2H).

Sources & evidence

ORD record
ord-306e5d28412d4aba8bd00ab8c0dfa50c
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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