Ethyl Acetate → HCID 23081384, compound

HRID 856024Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[O:13]1[C:17]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:10][C:9]([F:12])([F:11])[O:8][C:5]1[CH:6]=[CH:7][C:2]([N:20]2[CH2:21][CH2:22][C:17]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:18][CH2:19]2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-bromo-4-(trifluoromethoxy)-benzene (6.3 g, 26.14 mmol), 1,4-dioxa-8-azaspiro-[4,5]decane (3.35 ml, 26.14 mmol), palladium acetate (60 mg, 0.26 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (244 mg, 0.39 mmol), and sodium tert-butoxide (3.77 g, 39.23 mmol) in toluene (50 ml) was stirred at 80° C. for 1 hour. The reaction mixture was allowed to return to room temperature, to which ethyl acetate (50 ml) was added, and the resulting mixture was then filtered. The filtrate was washed with water and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1) to afford 8-(4-trifluoromethoxyphenyl)-1,4-dioxa-8-azaspiro[4,5]decane (6.54 g, yield 83%) as a pale yellow powder.

Workup

additionwas added
filtrationthe resulting mixture was then filtered
washThe filtrate was washed with water and brine
dry with materialdried over magnesium sulfate
filtrationAfter filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1)

Sources & evidence

ORD record: ord-ac4c272e894440f09ea68cc0531cab99
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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