Ethyl ketone → HCID 57849336, compound

HRID 736519Notes

Reaction equation

HRID 736519 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:22][CH3:23])([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[C:15]([CH3:21])[CH:14]=2)[CH2:11][CH3:12])=[CH:6][C:5]=1[CH3:24].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:36][CH2:37][C:38](=[O:41])[CH2:39][CH3:40]>>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:11][CH3:12])([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:38]([CH2:39][CH3:40])([OH:41])[CH2:37][CH3:36])=[C:15]([CH3:21])[CH:14]=2)[CH2:22][CH3:23])=[CH:6][C:5]=1[CH3:24]

Participants

4

Reactant 3

HCID 7288Ethyl ketoneHCID 2733832Lithium HexamethyldisilazideHCID 57849361HCID 57849361, compound

Product 1

HCID 57849336HCID 57849336, compoundYield 71%

Procedure

4-[1-Ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-benzoic acid methyl ester (2.50 g, 7.47 mmol), lithium hexamethyldisilazide (8.22 ml, 8.22 mmol, 1.0 M in THF) and 3-pentanone (870 μL, 8.22 mmol) are reacted and purified analogous to Example 1H to give the title compound (2.22 g, 71%).

Workup

  1. custompurified analogous to Example 1H

Sources & evidence

ORD record
ord-65cd6bb28c194628a5d859b4a3a195cb
Source dataset
uspto-grants-2009_09
Patent number
US07595345B2

Reaction notes

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