Methyl 3-(4-iodophenyl)propanoate → HCID 58319105, compound

HRID 2043017Notes

Reaction equation

HRID 2043017 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])#[CH:15]>>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]#[C:15][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 554150Methyl 3-(4-iodophenyl)propanoateHCID 5829121-Ethynyl-2-methoxybenzene

Product 1

HCID 58319105HCID 58319105, compound

Procedure

The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (90 mg, 0.31 mmol) and 1-ethynyl-2-methoxybenzen (40 μL, 0.31 mmol) according to the general procedure IC to give 86 mg (94%) of a pure orange-brown oil. Rf=0.44 (EtOAc:PE; 1:2); 1H NMR (CDCl3): δ 7.48 (d, J=8.1 Hz, 3H) 7.29-7.22 (m, 1H) 7.16 (d, J=8.2, 2H) 6.95-6.88 (m, 2H) 3.90 (s, 3H) 3.66 (s, 3H) 2.95 (t, J=7.6 Hz, 2H) 2.63 (t, J=7.6 Hz, 2H); 13C NMR (CDCl3): δ 173.3, 160.1, 140.8, 133.7, 132.0, 129.8, 128.4, 121.7, 120.6, 112.7, 110.9, 93.5, 85.6, 56.0, 51.8, 35.6, 31.0; ESI-MS m/z 317.0 (M+Na+).

Sources & evidence

ORD record
ord-0c79bd090ed04bb6aa6e8d2ee6b5e740
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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