Phenylacetylene → HCID 12718991, compound

HRID 387410Notes

Reaction equation

HRID 387410 reaction equation
[N:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)=[N+:2]=[N-:3].[C:14]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C[C-]1C(C)=C(C)C(C)=C1C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru+].C1COCC1>[C:4]12([N:1]3[C:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:21][N:3]=[N:2]3)[CH2:5][CH:6]3[CH2:12][CH:10]([CH2:9][CH:8]([CH2:7]3)[CH2:13]1)[CH2:11]2

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 3571141-Azidoadamantane

Product 1

HCID 12718991HCID 12718991, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 71310463Chlororuthenium(1+) 1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-ide--triphenylphosphane (1/1/2)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-Azidoadamantane (177 mg, 1 mmol), phenylacetylene (113 mg, 1.1 mmol), Cp*RuCl(PPh3)2 (8 mg, 0.01 mmol, 1 mol %). Solvent: THF, 10 mL, 60° C., 12 hours. Product obtained as off-white powder in 52% yield (145 mg). ESI-MS: m/z 280, [M+H].

Workup

  1. customProduct obtained as off-white powder in 52% yield (145 mg)

Sources & evidence

ORD record
ord-cfde0d56c68f4aee919de632624f266b
Source dataset
uspto-grants-2013_02
Patent number
US08372986B2

Reaction notes

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