Isopropyl iodide → HCID 21107173, compound

HRID 1869970Notes

Reaction equation

HRID 1869970 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][C:7]2([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].I[CH:28]([CH3:30])[CH3:29]>CC(C)=O>[CH3:14][C:7]1([CH3:13])[C:6]2[C:11](=[C:2]([O:1][CH:28]([CH3:30])[CH3:29])[CH:3]=[C:4]([C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=2)[C:10](=[O:12])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 21107256HCID 21107256, compound2×

Product 1

HCID 21107173HCID 21107173, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 8-hydroxy-4,4-dimethyl-6-trimethylsilanylethynyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 66, 0.32 g, 1.12 mmol) in acetone (20 mL) was treated with potassium carbonate (0.773 g, 5.6 mmol) and 2-iodopropane (2 g, 11.76 mmol) and the resulting reaction mixture was refluxed for 3 days. It was cooled to ambient temperature, the solids were filtered off and the filtrate was evaporated in vacuo to an oil that was subjected to flash column chromatography over silica gel (230-400 mesh) using 2-6% ethyl acetate in hexane as the eluent to afford the title product as (0.055 g, 15%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 3 days
  3. filtrationthe solids were filtered off
  4. customthe filtrate was evaporated in vacuo to an oil that

Sources & evidence

ORD record
ord-5d0d9a37e1664bcabfd97764b5c76438
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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