1-Phenyl-1-propanone → HCID 78135731, compound

HRID 626124Notes

Reaction equation

HRID 626124 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:26]=[CH:25][C:11]([O:12][CH:13]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[C:29]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)[CH2:30][CH3:31]>>[C:33]1([C:29]([CH2:30][CH3:31])=[C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:28][CH:27]=2)[C:8]2[CH:9]=[CH:10][C:11]([O:12][CH:13]3[CH2:17][CH2:16][NH:15][CH2:14]3)=[CH:25][CH:26]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 89672892HCID 89672892, compound

Product 1

HCID 78135731HCID 78135731, compoundYield 86%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, tert-butyl 3-(4-(4-hydroxybenzoyl)phenoxy)pyrrolidine-1-carboxylate (395 mg, 1.03 mmol) was reacted with propiophenone (276 mg, 2.06 mmol) to give 340 mg desired product (86% yield, Z/E=1/1) as a light yellow solid. m/z=386[M+1]+.

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-05d040ced5aa4ca48a8e4637b390e3a7
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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