Ethanol → HCID 58883474, compound

HRID 1870037Notes

Reaction equation

HRID 1870037 reaction equation
[CH3:1][C:2]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:8]=2)[C:3]=1OS(C(F)(F)F)(=O)=O.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:3]1[C:4]2[C:9](=[CH:8][C:7]([C:14]#[C:15][Si:16]([CH3:18])([CH3:17])[CH3:19])=[CH:6][CH:5]=2)[C:10]([CH3:12])([CH3:13])[CH2:11][C:2]=1[CH3:1])=[O:60])[CH3:63]

Participants

9

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 86600379HCID 86600379, compound2×

Product 1

HCID 58883474HCID 58883474, compound

Reagents, catalysts & solvents 4

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

Procedure

Following General Procedure E and using trifluoro-methanesulfonic acid 2,4,4-trimethyl-6-trimethylsilanylethynyl-3,4-dihydro-naphthalen-1-yl ester (Intermediate 198, 1.59 g, 3.8 mmol), palladium acetate (0.1 g, 0.45 mmol), 1,3-bis(diphenylphosphino)propane (0.1 g, 0.24 mmol), N,N-dimethylformamide (2.4 mL), ethanol (2.4 mL) and triethyl amine (2.4 mL) followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent the title compound was obtained (0.31 g, 24%) as a yellow oil.

Sources & evidence

ORD record
ord-e58ce8611c904b409cc1e627ea303df6
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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