1,2-Dimethoxyethane → HCID 59192526, compound

HRID 2384000Notes

Reaction equation

HRID 2384000 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[C:11](Br)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(COC)OC>O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6](=[O:21])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 59192521(3-Bromo-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester

Product 1

HCID 59192526HCID 59192526, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of (3-bromo-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (XIIIb, 78 mg, 0.22 mmol), phenylboronic acid (55.3 mg, 0.44 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (24.1 mg, 0.033 mmol), and cesium carbonate (144.8 mg, 0.44 mmol) was added dimethoxyethane (2 mL) at room temperature under nitrogen. The resulting brown reaction mixture was heated at 95° C. for 15 h. Then, the reaction mixture was cooled to room temperature, and diluted with water (20 mL) and ethyl acetate (20 mL). The aqueous layer was separated and extracted with ethyl acetate (20 mL), and the combined organic extracts were washed with water (50 mL) and brine solution (50 mL), then dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the colored residue. Chromatography using an ISCO (12 g) column, (gradient elution with 2-25% ethyl acetate in hexanes) afforded (5-oxo-3-phenyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (54 mg, 70%) as a white solid: ES(+)-HRMS m/e calcd. for C22H24O4 (M+Na)+375.1567, obsd. 375.1567.

Workup

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (20 mL)
  4. washthe combined organic extracts were washed with water (50 mL) and brine solution (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto provide the colored residue
  9. washan ISCO (12 g) column, (gradient elution with 2-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8c4ac9b1aa354ddbbf176eda4a032408
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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