2,2,6-Trimethylcyclohexanone → 2-Ethynyl-1,3,3-trimethylcyclohex-1-ene

HRID 1603271Notes

Reaction equation

[Si]([C:5]#[CH:6])(C)(C)C.[CH3:7][C:8]1([CH3:16])[CH2:13][CH2:12][CH2:11][CH:10]([CH3:14])[C:9]1=O.CC[N+](S(/N=C(/OC)\[O-])(=O)=O)(CC)CC.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:10]([C:9]1[C:8]([CH3:16])([CH3:7])[CH2:13][CH2:12][CH2:11][C:5]=1[CH3:6])#[CH:14]

Participants

Reactant 4

HCID 170002,2,6-Trimethylcyclohexanone

HCID 66111Trimethylsilylacetylene

HCID 2724141Tetrabutylammonium Fluoride

HCID 9566069Methyl-N-(triethylammoniumsulfonyl)carbamate

Product 1

HCID 132969122-Ethynyl-1,3,3-trimethylcyclohex-1-ene

Procedure

The prerequisite 2-ethynyl-1,3,3-trimethyl-1-cyclohexene was synthesized according to standard procedures by addition of the Li-derivative of TMS-acetylene to 2,2,6-trimethylcyclohexanone, dehydration by treatment with Burgess-reagent (methoxy-carbonylsulfamoyl-triethylammonium hydroxide, inner salt), and finally desilyation with tetrabutylammonium fluoride. It has to be used immediately due to its instability.

Sources & evidence

ORD record: ord-18fd6c4baf294af594d496449e704a64
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05986131

Reaction notes

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