(2E)-3-{4-[Cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenamide → 4-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenol

HRID 1716015Notes

Reaction equation

HRID 1716015 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=C2CCOCC2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C1(=C(C2C=CC(O)=CC=2)C2C=CC(/C=C/C(N)=O)=CC=2)CCCCC1.[CH3:47][C:48]1([CH3:57])[CH2:53][C:52](=O)[CH2:51][C:50]([CH3:56])([CH3:55])[O:49]1>[Zn].Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[C:52]2[CH2:53][C:48]([CH3:57])([CH3:47])[O:49][C:50]([CH3:56])([CH3:55])[CH2:51]2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11256079(2E)-3-{4-[Cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenamideHCID 118296912,2,6,6-Tetramethyloxan-4-oneHCID 686541974-[(4-Bromophenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenol

Product 1

HCID 686543254-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenolYield 76%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalyst

Procedure

Following the procedure described for compound 46, zinc powder (0.957 g, 14.6 mmole), TiCl4 (0.800 mL, 7.30 mmole), (4-bromophenyl)(4-hydroxyphenyl)methanone (2) (0.512 g, 1.85 mmole) and 2,2,6,6-tetramethyltetrahydro-4H-pyran-4-one (52) (0.851 mL, 5.45 mmole), afforded 0.564 g (76%) of 53 as a white foamy solid. 1H NMR (CDCl3): δ 7.41 (d, J=8.3 Hz, 2H), 7.02 (d, J=8.4 Hz, 2H), 7.01 (d, J=8.4 Hz, 2H), 6.76 (d, J=8.3 Hz, 2H), 4.99 (s, 1H), 2.24 (s, 2H), 2.20 (s, 2H), 1.22 (s, 6H), 1.21 (s, 6H).

Sources & evidence

ORD record
ord-63436bbf6112488a914d769c402d6c7d
Source dataset
uspto-grants-2010_09
Patent number
US07799828B2

Reaction notes

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