Methanesulfonic Acid → Methyl 3-[4-(benzyloxy)-2-methoxyphenyl]-3-cyanopropanoate

HRID 922261Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:20]#[N:21])[CH2:16][C:17]([OH:19])=[O:18])=[C:11]([O:22][CH3:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]S(O)(=O)=O>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:20]#[N:21])[CH2:16][C:17]([O:19][CH3:24])=[O:18])=[C:11]([O:22][CH3:23])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged with methanol (10 mL). To the stirred solvent was added 3-[4-(benzyloxy)-2-methoxyphenyl]-3-cyanopropanoic acid (0.62 g, 2.56 mmol) and methane sulfonic acid (1 mL), it was heated at 65° C. for 2 h. The RM was concentrated, extracted with ethyl acetate (50 mL×2). The organic layer was washed with water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as brown liquid. (0.65 g, yield: 100.0%).

Workup

customTo a 25 mL RB flask fitted with magnetic stirrer
concentrationThe RM was concentrated
extractionextracted with ethyl acetate (50 mL×2)
washThe organic layer was washed with water (50 mL) and saturated brine solution (50 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
customthe solvent was removed under reduced pressure
customThe product was obtained as brown liquid

Sources & evidence

ORD record: ord-4831c0c1421a4a879386cae56df5cf58
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278915B2

Reaction notes

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