2-Cyclohexenone, 5,5-dimethyl- → HCID 22904120, compound

HRID 1489203Notes

Reaction equation

HRID 1489203 reaction equation
CC1(C)CC(=O)C=CC1.C(C1C=CC=CC=1C(Br)O[SiH](C)C)(C)(C)C.[CH2:26]=[C:27]1[CH2:32][CH2:31][CH2:30][C:29]([CH3:34])([CH3:33])[CH:28]1[CH2:35][C:36]1[CH:41]=[C:40](OC)[C:39](Br)=[CH:38][C:37]=1[OH:45]>>[CH2:26]=[C:27]1[CH:28]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[OH:45])[C:29]([CH3:34])([CH3:33])[CH2:30][CH:31]=[CH:32]1

Participants

4

Reactant 3

HCID 1383222-Cyclohexenone, 5,5-dimethyl-HCID 10593144HCID 10593144, compoundHCID 131720236HCID 131720236, compound

Product 1

HCID 22904120HCID 22904120, compound

Procedure

This compound was prepared from 5,5-dimethylcyclohex-2-en-1-one (11) and 2-(tert-butyl)dimethylsilyloxybenzyl bromide (9) in three steps in the manner previously described for the synthesis of olefin 16, affording the desired phenol as a colorless oil. 1H NMR (400MHz, CDCl3) δ0.90 and 1.15 (2s, 2×3H, geminal-CH3 's), 1.85 and 2.24 (d of ABq, 2H, JAB =18.8 Hz, JA =5,5 Hz, JB =0 Hz, 4-H), 2.06 (dd, 1H, J=11.4, 3.2 Hz, 6-H), 3.30 and 2.88 (d of ABq, 2H, JAB =13.5 Hz, JA =11.4 Hz, JB =3.4 Hz, benzylic-CH2), 4.20 and 4.69 (2s, 2×1H, methylidene-CH2), 4.61 (s, 1H, OH), 5.77 (ddd, 1H, J=7.8, 5.4, 5.4 Hz, 3-H), 6.09 (dd, 1H, J=7.5, 2.2 Hz, 2-H), 6.75 (dd, 1H, J=7.1, 0.8 Hz, 3'-H), 6.82 (ddd, 1H, J=8.4, 7.3, 1.1 Hz, 5'-H), 6.97 (dd, 1H, J=5.9, 1.5 Hz, 6'-H), 7.05 ppm (ddd, 1H, J=9.3, 7.8, 1.7 Hz, 4'H). [Compound 34 is hereinafter also referred to as COMPOUND "C" or 120363]

Sources & evidence

ORD record
ord-ecad22e72c744d3db06516d135703a79
Source dataset
uspto-grants-1997_10
Patent number
US05677336

Reaction notes

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