Tetrahydrofuran → HCID 57707908, compound

HRID 216756Notes

Reaction equation

HRID 216756 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH:18]=[O:19])=[CH:16][C:15]2[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1.[CH2:21]1[CH2:25]OC[CH2:22]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH:18]([OH:19])[CH2:25][CH:21]=[CH2:22])=[CH:16][C:15]2[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 57708005HCID 57708005, compound

Product 1

HCID 57707908HCID 57707908, compound

Conditions

Temperature
0 °C

Procedure

Prepared according to procedure K: To a solution of 2-(2-chlorophenyl)-8-methylquinoline-3-carbaldehyde (1.4 g, 5 mmol) in THF (20 mL) at 0° C. under N2 was added dropwise a solution of allylmagenisiumbromide (1M, 1.1 eq, 5.5 mL) in THF and the mixture was stirred at 0° C. for 2 h. The mixture was partitioned between EtOAc (50 mL) and H2O (30 mL), the layers were separated, the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were dried (Na2SO4), concentrated and purified by flash chromatography (0% to 25% EtOAc/hexane) to provide 1-(2-(2-chlorophenyl)-8-methyl-quinolin-3-yl)but-3-en-1-ol as a colorless oil. 1H-NMR (CDCl3) δ 8.45 (s, major, 1H), 8.40 (s, minor, 1H), 7.77 (d, J=7.9 Hz, 1H), 7.43-7.60 (m, 6H), 5.56-5.73 (m, 1H), 4.96-5.17 (m, 2H), 4.80-4.84 (m, 1H), 2.80 (s, 3H), 2.34-2.59 (m, 2H). Mass Spectrum (ESI) m/e=324 (M+1).

Workup

  1. customPrepared
  2. customThe mixture was partitioned between EtOAc (50 mL) and H2O (30 mL)
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×30 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by flash chromatography (0% to 25% EtOAc/hexane)

Sources & evidence

ORD record
ord-4480b93da374416bb81be7eecb01314f
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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