Benzene, 1-bromo-3-ethyl- → 6-(3-ethylphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

HRID 1453340Notes

Reaction equation

HRID 1453340 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[CH:3]=1.BrC1C=CC(C(C)C)=C(F)C=1.[CH:21]1([C:26]([OH:39])([C:37]#[CH:38])[CH2:27][C:28]2[O:33]C(C)(C)O[C:30](=[O:36])[CH:29]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH:21]1([C:26]2([CH2:37][CH2:38][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[CH:3]=3)[O:39][C:30](=[O:36])[CH2:29][C:28](=[O:33])[CH2:27]2)[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 3

HCID 123170Benzene, 1-bromo-3-ethyl-HCID 210510924-Bromo-2-fluoro-1-(1-methylethyl)benzeneHCID 224998026-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one

Product 1

HCID 160761086-(3-ethylphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Procedure

The title compound was prepared analogously to Example A(64), where 1-Bromo-3-ethyl-benzene was substituted in place of 4-bromo-2-fluoro-1-isopropylbenzene of that example and Enantiomer B of 6-(2-cyclopentyl-2-hydroxybut-3-ynyl)-2,2-dimethyl-4H-1,3-dioxin-4-one was used in place of the racemic alkyne. 1H NMR (CDCl3): δ 1.23 (t, 3H, J=7.6 Hz), 1.50-1.83 (br m, 8H), 1.91-2.05 (m, 2H), 2.29 (m, 1H), 2.59-2.68 (m, 4H) 2.27, (s, 2H), 3.42 (s, 2H), 6.96 (m, 2H), 7.06 (d, 1H, J=7.01 Hz), 7.21 (t, 1H, J=8.0 Hz). ESIMS: MH+ 315.20, MH− 313.20.

Sources & evidence

ORD record
ord-5442726f58394d18959a65cc31266ada
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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