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

HRID 1768093Notes

Reaction equation

HRID 1768093 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) is 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 is stirred at 70° C. After 12 hours, the same work-up procedure as in Example 1 yields 70 mg (70%) of 4-(3-cinnamyloxy-4-methoxyphenyl)-2-pyrrolidone:

Sources & evidence

ORD record
ord-e30f42f71e4140f0a46f5bd6f674d449
Source dataset
uspto-grants-2007_06
Patent number
US07235579B2

Reaction notes

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