Sodium hydride → HCID 21707624, compound

HRID 1275946Notes

Reaction equation

[CH3:1][C:2](=[CH:6][CH2:7][CH:8]1[CH2:12][CH:11]=[C:10]([CH3:13])[C:9]1([CH3:15])[CH3:14])[C:3](=[O:5])[CH3:4].[I-].[CH3:17][S+](C)(C)=O.[H-].[Na+]>>[CH3:1][C:2]1([C:3](=[O:5])[CH3:4])[CH2:17][CH:6]1[CH2:7][CH:8]1[CH2:12][CH:11]=[C:10]([CH3:13])[C:9]1([CH3:15])[CH3:14]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

HCID 1032103-Penten-2-one, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-

Product 1

HCID 21707624HCID 21707624, compoundYield 45%

Procedure

11.3 g (55 mmol) of 3-methyl-5-(2,2,3-trimethylcyclopent-3-enyl)-pent-3-en-2-one was cyclopropanated with 14.1 g (63 mmol) of trimethylsulfoxonium iodide and 3.08 g (64 mmol) of 50% oil suspension of sodium hydride according to Example 11a giving 5.4 g (45% yield) of 1-[1-methyl-2-(2,2,3-trimethylcyclopent-3-enylmethyl)cyclopropyl]ethanone.

Sources & evidence

ORD record: ord-dbe3cafa1a78473689cb540d4418b1cb
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06162954

Reaction notes

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