tert-Butyl acrylate → tert-butyl 3-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[C:11]1[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=1.[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[CH:18]=[CH2:19]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:19][CH2:18][C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:4][C:3]=1[C:11]1[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=1Participants
3
Procedure
Triton-B (0.4 ml, 0.88 mmol) was added to a stirred mixture of 2-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenyl)ethanol [Example 13, Step iii)] (1.7 g) and tert-butyl acrylate (8 mL). The mixture was stirred at room temperature over 1 h. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane to afford tert-butyl 3-(4-fluoro-3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoate (2.65 g) as a colorless liquid. MS [M+H-C4H8]+=293 (MultiMode+) 1H NMR (300 MHz, CDCl3) δ 7.84 (s, 1H), 7.77 (d, J=2.5 Hz, 1H), 7.40-7.35 (m, 1H), 7.05-6.98 (m, 2H), 3.96 (s, 3H), 3.69 (t, J=6.4 Hz, 2H), 3.66 (t, J=6.9 Hz, 2H), 2.86 (t, J=6.9 Hz, 2H), 2.48 (t, J=6.4 Hz, 2H), 1.43 (s, 9H)
Workup
- customThe crude product was purified by flash silica chromatography, elution gradient 0 to 100% ethyl acetate in isohexane
Sources & evidence
- ORD record
- ord-8e07d9bffe1848d3b306eef5409a2c99
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017602B2
Reaction notes
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