6-(2,2-Dichlorovinylsulphonyl)-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene → 6-Ethynylsulphonyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

HRID 1278837Notes

Reaction equation

HRID 1278837 reaction equation
Cl[C:2](Cl)=[CH:3][S:4]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[C:13]([CH3:19])([CH3:18])[CH2:12][CH2:11][C:10]2([CH3:21])[CH3:20])(=[O:6])=[O:5].C([Li])CCC.CCCCCC>C1COCC1>[C:3]([S:4]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[C:13]([CH3:19])([CH3:18])[CH2:12][CH2:11][C:10]2([CH3:21])[CH3:20])(=[O:6])=[O:5])#[CH:2]

Participants

4

Reactant 2

HCID 223478376-(2,2-Dichlorovinylsulphonyl)-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 178418244HCID 178418244, compound

Product 1

HCID 223478256-Ethynylsulphonyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that of Example 5(b), by reaction at −78° C. of 6-(2,2-dichlorovinylsulphonyl)-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (8 g, 24.3 mmol) in 200 ml of THF with 2.5 M n-butyllithium/hexane (21.4 ml, 53.5 mmol), 2.08 g (33%) of the expected alkyne are obtained in the form of a yellow solid.

Workup

  1. customare obtained in the form of a yellow solid

Sources & evidence

ORD record
ord-c3e2a20a916e488a8da0401e7fe8f44a
Source dataset
uspto-grants-2002_09
Patent number
US06444709B1

Reaction notes

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