Propargyl bromide → 2-Methyl-2-propargyl-5-methoxy-6,7-dichloro-1-indanone

HRID 1287448Notes

Reaction equation

HRID 1287448 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15].[H-].[Na+].[CH2:18](Br)[C:19]#[CH:20]>COCCOC>[CH3:1][C:2]1([CH2:20][C:19]#[CH:18])[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 123955612-Methyl-5-methoxy-6,7-dichloro-1-indanone

Product 1

HCID 203584432-Methyl-2-propargyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Methyl-2-propargyl-5-methoxy-6,7-dichloro-1-indanone is prepared by following substantially the same procedure described in Example 4, Step B, using the following reagents: 2-methyl-5-methoxy-6,7-dichloro-1-indanone (14.7 g., 0.06 mole), sodium hydride (1.72 g., 0.072 mole), 1,2-dimethoxyethane (500 ml.) and propargyl bromide (8 ml.). The above procedure gives 16.5 g. (97%) of 2-methyl-2-propargyl-5-methoxy-6,7-dichloro-1-indanone which after recrystallization from methyl cyclohexane melts at 118°C.

Workup

  1. customThe above procedure gives 16.5 g
  2. custom(97%) of 2-methyl-2-propargyl-5-methoxy-6,7-dichloro-1-indanone which after recrystallization from methyl cyclohexane melts at 118°C.

Sources & evidence

ORD record
ord-8834a15e218a4e789204cf4b6cec534e
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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