3-Phenylprop-2-En-1-Ol → HCID 68683012, compound

HRID 731760Notes

Reaction equation

HRID 731760 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:17]=[C:18]([CH:24]2[CH2:28][NH:27][C:26](=[O:29])[CH2:25]2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].[CH2:30](O)[CH:31]=[CH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:30]([O:15][C:16]1[CH:17]=[C:18]([CH:24]2[CH2:28][NH:27][C:26](=[O:29])[CH2:25]2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH:31]=[CH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 3083-Phenylprop-2-En-1-OlHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10130484HCID 10130484, compound

Product 1

HCID 68683012HCID 68683012, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Diisopropylazodicarboxylate (61 mg, 0.6 mmol) was added to a solution of 4-(3-hydroxy-4-methoxyphenyl)-2-pyrrolidone (63 mg, 0.3 mmol), cinnamyl alcohol (43 mg, 0.3 mmol) and triphenyl phosphine (157 mg, 0.6 mmol) in 3 mL of tetrahydrofuran and the reaction mixture was stirred at 70° C. After 12 hours, the same work-up procedure as described in Example 1 gave 70 mg (70%) of 4-(3-cinnamyloxy-4-methoxyphenyl)-2-pyrrolidone: 1H NMR (300 MHz, CDCl3) δ 7.40 (d, J=6.8 Hz, 2H), 7.31 (t, J=6.8 Hz, 2H), 7.25 (d, J=7.2 Hz, 1H), 6.86-6.81 (m, 2H), 6.71 (d, J=15.6 Hz, 1H), 6.42 (m, 1H), 5.92 (b, 1H), 4.76 (dd, J=6.0, 1.2 Hz, 2H), 3.87 (s, 3H), 3.71 (t, J=8.8 Hz, 1H), 3.64-3.56 (m, 1H), 3.35 (t, J=8.8 Hz, 1H).

Sources & evidence

ORD record
ord-8bab3db5f3a8478fbdabd1bb44b8cf29
Source dataset
uspto-grants-2009_09
Patent number
US07585882B2

Reaction notes

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