Sulfoxonium, trimethyl-, iodide (1:1) → (3-(Benzyloxy)phenyl)(2-methylcyclopropyl)methanone

HRID 1662570Notes

Reaction equation

HRID 1662570 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:19])/[CH:16]=[CH:17]/[CH3:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[CH3:21][S+](C)(C)=O.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH:16]2[CH2:18][CH:17]2[CH3:21])=[O:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57706211(E)-1-(3-(Benzyloxy)phenyl)but-2-en-1-one

Product 1

HCID 57706540(3-(Benzyloxy)phenyl)(2-methylcyclopropyl)methanoneYield 36.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 93.C (5.33 g, 21.1 mmol) in ACN (200 mL) were added trimethylsulfoxonium iodide (available from Aldrich) (5.58 g, 25.3 mmol) and DBU (4.11 mL, 27.5 mmol). The mixture was stirred overnight at 60° C. under N2, cooled to room temperature, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 93.D (2.04 g, 36% yield) as a colorless oil.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-73e4047b6c164f9caaee95197e9161f1
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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