Diethyl Ether → HCID 57871419, compound

HRID 550216Notes

Reaction equation

HRID 550216 reaction equation
[CH2:1]([C:3]([C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[CH:14]2)=[CH:9][CH:8]=1)([OH:6])[CH2:4][CH3:5])[CH3:2].CCN(CC)CC.[C]=[O:33].C[CH2:35][O:36][CH2:37]C>CO.CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:35][O:36][C:37]([C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][C:7]([C:3]([CH2:4][CH3:5])([OH:6])[CH2:1][CH3:2])=[CH:8][CH:9]=2)[CH:14]=1)=[O:33]

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 57871420HCID 57871420, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 57871419HCID 57871419, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

Treat a mixture of trifluoromethanesulfonic acid 7-(1-ethyl-1-hydroxypropyl)naphthalen-2-yl ester (1.0 g, 2.76 mmol), Pd(OAc)2 (0.062 g, 0.27 mmol), bis-(diphenylphosphino)ferrocene (0.14 g, 0.25 mmol), Et3N (2.0 mL, 14.3 mmol) in MeOH (10 mL) and DMSO (15 mL) with carbon monoxide at 100 psi at 80° C. for 4 h. Pour the reaction mixture into ether (100 mL) and wash the resulting solution with brine (4×50 mL). Add EtOAc (100 mL), wash the organic layer with brine. Dry the organic layer over Na2SO4, filter, and concentrate the filtrate. Purify by silica gel radial chromatography (5:95 to 15:85 EtOAc:hex) to give the title compound as a yellow oil (0.71 g, 94%). 1H NMR (400 MHz, CDCl3) δ 0.792 (t, J=7.5 Hz, 6H), 1.80-2.04 (m, 4H), 4.00 (s, 3H), 7.58 (dd, J=8.8, 1.4 Hz, 1H), 7.80-7.87 (m, 2H), 7.99 (d, J=1.3 Hz, 1H), 8.02 (d, J=1.8 Hz, 1H), 8.05 (d, J=1.8 Hz, 1H), 8.61 (d, J=1.0 Hz, 1H).

Workup

  1. additionTreat
  2. washwash the resulting solution with brine (4×50 mL)
  3. washAdd EtOAc (100 mL), wash the organic layer with brine
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate the filtrate
  7. customPurify by silica gel radial chromatography (5:95 to 15:85 EtOAc:hex)

Sources & evidence

ORD record
ord-290f17ac18f34ab7b751d413f06c6663
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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