1-Cyclohexenyl trifluoromethanesulfonate → 1-Cyclohex-1-enyl-2-isopropyl-4-methoxy-benzene

HRID 237818Notes

Reaction equation

HRID 237818 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[C:5]([CH:12]([CH3:14])[CH3:13])[CH:4]=1.S(O[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1)(C(F)(F)F)(=O)=O>>[CH:23]1([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH:12]([CH3:14])[CH3:13])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[C:23]1([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH:12]([CH3:14])[CH3:13])[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

4

Reactant 2

HCID 3194401-Cyclohexenyl trifluoromethanesulfonateHCID 220217692-Isopropyl-4-methoxyphenyl boronic acid

Product 2

HCID 685292601-Cyclohex-1-enyl-2-isopropyl-4-methoxy-benzeneHCID 68529356Cyclohexyl-4-methoxy-2-isopropyl-benzene

Procedure

Cyclohexyl-4-methoxy-2-isopropyl-benzene was prepared in two steps by a Suzuki coupling of 4-methoxy-2-isopropyl-phenylboronic acid and cyclohexenol triflate following the procedures of Carmen et. al., Synlett 2005, No. 10, pp 1601-1605, to obtain 1-cyclohex-1-enyl-2-isopropyl-4-methoxy-benzene, which was subsequently hydrogenated (Pd/C, H2, MeOH) to form 1-cyclohexyl-4-methoxy-2-isopropyl-benzene.

Sources & evidence

ORD record
ord-e6a36dbe029b450e83c3f8c4e7ba5dac
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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