Ethanol → HCID 58883454, compound

HRID 1870030Notes

Reaction equation

HRID 1870030 reaction equation
[C:1]([Si:5]([CH3:29])([CH3:28])[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[C:13](OS(C(F)(F)F)(=O)=O)=[CH:12][CH2:11][C:10]2([CH3:27])[CH3:26])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)[CH:61]=[O:62].[CH2:64]([OH:66])[CH3:65]>CCCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:64]([O:66][C:61]([C:13]1[C:14]2[C:9](=[CH:8][C:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([CH3:28])[CH3:29])=[C:16]([CH3:17])[CH:15]=2)[C:10]([CH3:27])([CH3:26])[CH2:11][CH:12]=1)=[O:62])[CH3:65]

Participants

9

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 86600200HCID 86600200, compound2×

Product 1

HCID 58883454HCID 58883454, compound

Reagents, catalysts & solvents 4

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

Procedure

Following General Procedure E and using trifluoro-methanesulfonic acid 6-(tert-butyl-dimethyl-silanyloxy)-4,4,7-trimethyl-3,4-dihydro-naphthalen-1-yl ester (Intermediate 189, 3.4 g, 7.55 mmol), palladium acetate (0.36 g, 1.62 mmol), 1,3-bis(diphenylphosphino)propane (0.36 g, 0.86 mmol), N,N-dimethylformamide (7 mL), ethanol (7 mL) and triethyl amine (7 mL) followed by flash column chromatography over silica gel (230-400 mesh) using 7% ethyl acetate in hexane as the eluent the title compound was obtained (1.35 g, 48%).

Sources & evidence

ORD record
ord-fbaef39479ba4d6dbd4b0bce5c971ed0
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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