4,4-Dimethylpent-1-yn-3-ol → 1-{4-[1-(4-Benzyloxy-3-methylphenyl)-1-ethylpropyl]-phenyl}-4,4-dimethylpent-1-YN-3-OL

HRID 250180Notes

Reaction equation

HRID 250180 reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[CH:3]([OH:6])[C:4]#[CH:5].Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[CH:22]=[CH:23][C:24]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:25]([CH3:27])[CH:26]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][CH:11]=1>>[CH2:29]([O:28][C:24]1[CH:23]=[CH:22][C:21]([C:16]([C:13]2[CH:12]=[CH:11][C:10]([C:5]#[C:4][CH:3]([OH:6])[C:2]([CH3:8])([CH3:7])[CH3:1])=[CH:15][CH:14]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:26][C:25]=1[CH3:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 49144984,4-Dimethylpent-1-yn-3-olHCID 66891782HCID 66891782, compound

Product 1

HCID 668905651-{4-[1-(4-Benzyloxy-3-methylphenyl)-1-ethylpropyl]-phenyl}-4,4-dimethylpent-1-YN-3-OL

Procedure

In a manner similar to that described for Example 1D, but replacing 2-methyl-3-butyn-2-ol with 4,4-dimethylpent-1-yn-3-ol, the title compound was prepared from 5-[1-(4-bromophenyl)-1-ethylpropyl]-2-benzyloxytoluene: 1H-NMR (CDCl3) δ 7.44-7.48 (2H, m), 7.37-7.42 (2H, m), 7.31-7.36 (3H, m), 7.14 (2H, d, J=8.6), 6.94 (1H, dd, J=2.3, 8.3), 6.90 (1H, d, J=2.3), 6.79 (1H, d, J=8.3), 5.05 (2H, s), 2.22 (3H, s), 2.07 (4H, q, J=7.3), 1.07 (9H, s), 0.62 (6H, t, J=7.3).

Sources & evidence

ORD record
ord-1e878d1594074114a001418d0ef7dd6e
Source dataset
uspto-grants-2011_01
Patent number
US07863298B2

Reaction notes

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