3-Bromo-1-(trimethylsilyl)-1-propyne → Methyl [6,7-dichloro-1-oxo-2-phenyl-2-(3-(trimethylsilyl)-2-propynyl)-5-indanyloxy]acetate

HRID 1156190Notes

Reaction equation

HRID 1156190 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]2=[O:12])=[CH:4][C:3]=1[O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].Br[CH2:26][C:27]#[C:28][Si:29]([CH3:32])([CH3:31])[CH3:30]>C1CCCCC1.C(Cl)Cl>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([CH2:26][C:27]#[C:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:8]2=[O:12])=[CH:4][C:3]=1[O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 6425893-Bromo-1-(trimethylsilyl)-1-propyneHCID 12774096Methyl (6,7-dichloro-1-oxo-2-phenyl-5-indanyloxy)acetate

Product 1

HCID 12774092Methyl [6,7-dichloro-1-oxo-2-phenyl-2-(3-(trimethylsilyl)-2-propynyl)-5-indanyloxy]acetateYield 74%

Reagents, catalysts & solvents 1

HCID 21916607Dichloromethane cyclohexaneSolvent

Procedure

Reaction of methyl (6,7-dichloro-1-oxo-2-phenyl-5-indanyloxy)acetate with 1-bromo-3-(trimethylsilyl)-2-propyne according to Example 1, STEP (b), affords the title compound, m.p. 125.5°-127° (from cyclohexane-methylene chloride) in 74% yield.

Sources & evidence

ORD record
ord-821c80682b2a44e883a66372506427cb
Source dataset
uspto-grants-1982_06
Patent number
US04334088

Reaction notes

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