Agn-PC-0nddf9 → (E)-ethyl 3-(3-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)phenyl)butanoate

HRID 628609Notes

Reaction equation

HRID 628609 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1)=O.[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:25][C:26]2[C:31]([CH3:33])([CH3:32])[CH2:30][CH2:29][CH2:28][C:27]=2[CH3:34])C=CC=CC=1>>[CH3:34][C:27]1[CH2:28][CH2:29][CH2:30][C:31]([CH3:33])([CH3:32])[C:26]=1/[CH:25]=[CH:1]/[C:3]1[CH:4]=[C:5]([CH:9]([CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 10950920Agn-PC-0nddf9HCID 54075039Ethyl 3-(3-formylphenyl)butanoate

Product 1

HCID 69035008(E)-ethyl 3-(3-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)phenyl)butanoate

Procedure

Coupling of ethyl 3-(3-formylphenyl)butanoate with Wittig reagent 24 following the method used in Example 1 gave (E)-ethyl 3-(3-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)phenyl)butanoate as a colorless oil. Yield (0.383 g, 81%): 1H NMR (500 MHz, CDCl3) δ 7.25 (m, 3H), 7.07 (m, 1H), 6.66 (dd, J=16.3, 0.68 Hz, 1H), 6.31 (d, J=16.3 Hz, 1H), 4.09 (q, J=7.0 Hz, 2H), 3.28 (m, 1H), 2.65-2.52 (m, 2H), 2.04 (t, J=6.2 Hz, 2H), 1.76 (s, 3H), 1.64 (m, 2H), 1.49 (m, 2H), 1.30 (d, J=6.9 Hz, 3H), 1.20 (t, J=7.0 Hz, 3H), 1.06 (s, 6H).

Sources & evidence

ORD record
ord-00ebb713e31a434082aad0d1a527287d
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

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