2-Dicyclohexylphosphino-2-(N,N-Dimethylamino)Biphenyl → {4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid ethyl ester

HRID 751488Notes

Reaction equation

HRID 751488 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[C:5]([O:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2(N(C)C)CC=CC=C2C2C=CC=CC=2)CCCCC1.Br[Zn][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53]>O1CCCC1.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH2:55]([O:54][C:52](=[O:53])[CH2:51][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[C:5]([O:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:4][CH:3]=1)[CH3:56]

Participants

6

Reactant 3

HCID 665453382-Dicyclohexylphosphino-2-(N,N-Dimethylamino)BiphenylHCID 692674567-Bromo-4-[2-(tetrahydropyran-2-yloxy)ethoxy]benzofuranHCID 178472539HCID 178472539, compound

Product 1

HCID 69268314{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid ethyl esterYield 54%

Reagents, catalysts & solvents 2

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Combine 7-Bromo-4-[2-(tetrahydropyran-2-yloxy)ethoxy]benzofuran (2.598 g, 7.61 mmol), bis(dibenzylideneacetone) palladium (0.461 g, 0.802 mmol), and 2-dicyclohexylphosphino-2-(N,N-dimethylamino)biphenyl (0.308 g, 0.783 mmol) in tetrahydrofuran (15 ml) under nitrogen. Add bromo(2-ethoxy-2-oxoethyl)zinc (2 equiv.), and heat the mixture at 80° C. for 16 hours. (Knochel, P.; Honed, P.; Eds. Organozinc Reagents: A Practical Approach; Oxford University Press, Inc: London, 1999). Cool the mixture to room temperature, filter through a silica plug eluting with ethyl ether, and concentrate. Purify by flash chromatography and elute with hexane:ethyl acetate to give 1.422 g (54%) of the title compound as an oil. Mass spectrum: electrospray (m/z) 265 (M++1-85).

Workup

  1. filtrationfilter through a silica plug
  2. washeluting with ethyl ether
  3. concentrationconcentrate
  4. customPurify by flash chromatography
  5. washelute with hexane

Sources & evidence

ORD record
ord-2c1085d664c841a6a9ad385d0d90530c
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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