Phenylacetone → HCID 67126101, compound

HRID 513993Notes

Reaction equation

HRID 513993 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C([Li])CCC.[C:15]1([CH2:21][C:22](=[O:24])[CH3:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:22]([CH3:23])([OH:24])[CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7678PhenylacetoneHCID 70118Benzene, 1-chloro-4-ethynyl-HCID 178418339Butyllithium

Product 1

HCID 67126101HCID 67126101, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-chloro-4-ethynylbenzene (3C) (1.75 mL, 12.81 mmol) in THF (40 mL) at 0° C. was added n-butyllithium (2.5 M in hexanes, 5.13 mL, 12.81 mmol) and stirred for 1 h. A solution of 1-phenylpropan-2-one (3B) (1.38 g, 10.25 mmol) in THF (5 mL) was added and the reaction mixture was warmed to room temperature overnight. The reaction mixture was quenched with saturated NH4Cl solution and extracted with diethyl ether (2×). The combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 3D as a yellow oil (2.29 g). 1H-NMR: 300 MHz, (CDCl3) δ 7.35-7.20 (m, 9H), 3.0 (AB quart, J=13.2, 9.9 Hz, 2H), 1.59 (s, 3 H).

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with diethyl ether (2×)
  3. dry with materialThe combined organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bc8c534d49374d0ba911bb12189afbd0
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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