Ethyl 2-butynoate → Ethyl 3-methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoate

HRID 1278838Notes

Reaction equation

HRID 1278838 reaction equation
[C:1]([S:3]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[C:12]([CH3:18])([CH3:17])[CH2:11][CH2:10][C:9]2([CH3:20])[CH3:19])(=[O:5])=[O:4])#[CH:2].[C:21]([O:26][CH2:27][CH3:28])(=[O:25])[C:22]#[C:23][CH3:24]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:24][C:23]([C:2]#[C:1][S:3]([C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:12]([CH3:18])([CH3:17])[CH2:11][CH2:10][C:9]([CH3:20])([CH3:19])[C:8]=2[CH:7]=1)(=[O:5])=[O:4])=[CH:22][C:21]([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 2

HCID 78043Ethyl 2-butynoateHCID 223478256-Ethynylsulphonyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 73884431Ethyl 3-methyl-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)pent-2-en-4-ynoateYield 27%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

In a manner similar to that of Example 5(c), by reaction of 6-ethynylsulphonyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (2.08 g, 151 mmol) in 60 ml of toluene with Pd(OAc)2 (70 mg, 0.3 mmol), TDMPP (140 mg) and ethyl 2-butynoate (2.05 g, 20.9 mmol), 1 g (27%) of the expected ester is obtained in the form of a brown oil.

Sources & evidence

ORD record
ord-9cc50d4bb3394f78bab015dc1b61bc69
Source dataset
uspto-grants-2002_09
Patent number
US06444709B1

Reaction notes

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