4-Methoxybenzaldehyde → HCID 58762471, compound

HRID 858719Notes

Reaction equation

HRID 858719 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.[Al+3].[Cl-].[Cl-].[Cl-]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[C:15]([CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)=[C:14]([OH:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 6451240Aluminum(III) ChlorideHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Product 1

HCID 58762471HCID 58762471, compound

Procedure

The title compound was prepared by coupling 6-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione from Step 1 of Example B(13), to 4-Methoxy-benzaldehyde using the AlCl3/reduction procedure described for Example B(13). 1H NMR (CDCl3): δ 1.45–1.85 (brm, 8H), 1.98 (m, 2H), 2.29 (t, J=7.6 Hz, 1H) 2.44–3.02 (m, 7H), 3.88 (s, 3H), 3.94 (s, 3H), 6.73–7.85 (m, 7H). ESIMS (MH+): 471.7.

Sources & evidence

ORD record
ord-3aae8c9c98024476958584915c6168c1
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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