Ethanol → HCID 58883464, compound

HRID 2377508Notes

Reaction equation

HRID 2377508 reaction equation
[CH3:1][C:2]1([CH3:27])[C:11]2[C:6](=[CH:7][C:8]([CH3:18])=[C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=2)[C:5](OS(C(F)(F)F)(=O)=O)=[CH:4][CH2:3]1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)[CH:59]=[O:60].[CH2:62]([OH:64])[CH3:63]>CCCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:62]([O:64][C:59]([C:5]1[C:6]2[C:11](=[CH:10][C:9]([C:12]#[C:13][Si:14]([CH3:16])([CH3:17])[CH3:15])=[C:8]([CH3:18])[CH:7]=2)[C:2]([CH3:1])([CH3:27])[CH2:3][CH:4]=1)=[O:60])[CH3:63]

Participants

9

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 86600198HCID 86600198, compound2×

Product 1

HCID 58883464HCID 58883464, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure E and using trifluoro-methanesulfonic acid 4,4,7-trimethyl-6-trimethylsilanylethynyl-3,4-dihydro-naphthalen-1-yl ester (Intermediate 183, 0.73 g, 1.75 mmol), palladium acetate (0.1 g, 0.45 mmol), 1,3-bis(diphenylphosphino)propane (0.1 g, 0.24 mmol), N,N-dimethylformamide (3.5 mL), ethanol (3.5 mL) and triethyl amine (3.5 mL) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent the title compound was obtained (0.435 g, 73%).

Sources & evidence

ORD record
ord-8b2ea9752b6a4b04b5ddf6d967b336a3
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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