2-Bromoanisole → HCID 18727003, compound

HRID 842776Notes

Reaction equation

HRID 842776 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[CH2:10]1[O:19][C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[O:12][CH2:11]1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:10]1[O:19][C:13]2([CH2:18][CH2:17][N:16]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[O:8][CH3:9])[CH2:15][CH2:14]2)[O:12][CH2:11]1

Participants

8

Reactant 4

HCID 113582-BromoanisoleHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 80271Tri-o-tolylphosphineHCID 23676156Sodium t-butoxide

Product 1

HCID 18727003HCID 18727003, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-bromoanisole (6.00 g, 32.08 mmol) and 4-piperidone ethylene ketal (5.54 g, 38.69 mmol) in toluene (250 mL) was treated with sodium tert-butoxide (4.40 g, 45.76 mmol), tri-o-tolylphosphine (411 mg, 1.35 mmol), and tris(dibenzylideneacetone)dipalladium(0) (295 mg, 0.32 mmol) at room temperature. The mixture was heated in an oil bath (100° C., 2 h). The mixture was diluted with ether and the organics washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flash chromatography on silica gel (20% ethyl acetate/hexane) afforded the title compound (19).

Workup

  1. washthe organics washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3dc28f120744478b3d8feae4172b78e
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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