Hydrochloric Acid → HCID 53834781, compound

HRID 247246Notes

Reaction equation

[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[CH:3]=[CH2:4].I[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CN(C)CCN(C)C.Cl>C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:9]=1)[CH:3]=[CH:4][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A stirred mixture of 3,3-dimethyl-4-(4-fluoro-3-phenoxybenzyloxy)but-1-ene (0.27 g), p-iodoanisole (0.21 g), palladium (II) diacetate (0.02 g), tri-o-toluylphosphine (0.054 g) and tetramethylethylenediamine (0.1 g) was heated at 160° C. for 24 hours. After cooling, the mixture was poured into dilute aqueous hydrochloric acid, and extracted into ethyl acetate, the extracts combined, washed with water, dried over anhydrous magnesium sulphate, and concentrated by evaporation of the solvent to yield a brown oil. The crude product was distilled through a kugelrohr apparatus to give 3,3-dimethyl-1-(4-methoxyphenyl)-4-(4-fluoro-3-phenoxybenzyloxy)but-1-ene (0.033 g), as an oil, containated by 30% of 3,3-dimethyl-2-(4-methoxyphenyl)-4-(4-fluoro-3-phenoxybenzyloxy)but-1-ene.

Workup

temperatureAfter cooling
extractionextracted into ethyl acetate
washwashed with water
dry with materialdried over anhydrous magnesium sulphate
concentrationconcentrated by evaporation of the solvent
customto yield a brown oil
distillationThe crude product was distilled through a kugelrohr apparatus

Sources & evidence

ORD record: ord-0a0137e3d86e4145bb0f0bdbb2e0a469
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04705900

Reaction notes

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