Isophorone → HCID 131720240, compound

HRID 1489201Notes

Reaction equation

[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[C:11]([C:15]1[C:20]([O:21][SiH:22]([CH3:24])[CH3:23])=[C:19]([Br:25])[C:18]([O:26][CH3:27])=[CH:17][C:16]=1[CH2:28]C1C(=O)C=CCC1(C)C)([CH3:14])([CH3:13])[CH3:12]>>[C:11]([C:15]1[C:20]([O:21][SiH:22]([CH3:23])[CH3:24])=[C:19]([Br:25])[C:18]([O:26][CH3:27])=[CH:17][C:16]=1[CH2:28][CH:9]1[C:2](=[O:1])[CH:3]=[C:4]([CH3:10])[CH2:5][C:6]1([CH3:8])[CH3:7])([CH3:14])([CH3:13])[CH3:12]

Participants

Reactant 2

HCID 6544Isophorone

HCID 178488804HCID 178488804, compound

Product 1

HCID 131720240HCID 131720240, compoundYield 60%

Procedure

This compound was prepared from isophorone (0.168 g, 1.22 mmol) in the manner previously described for enone 13, affording 0.342 g (60%) of the alkylation product (Rf 0.40, 2:1 hexanes/ethyl acetate) as a colorless, oily solid. 1H NMR (400 MHz, CDCl3) δ0.20 and 0.22 [2s, 2×3H, Si(CH3)2 ], 0.99 [s, 9H, SiC(CH3)3 ], 1.00 and 1.02 (2s, 2×3H, geminal-CH3 's),b 1.91 (s, 3H, 3-CH3), 2.18 and 2.28 (ABq, 2H), 2.42 (dd, 1H), 2.82 (dd, 2H), 3.70 (s, 3H, OCH3), 5.82 (sl d, 1H, 2-H), 6.71 (s, 1H, 6'-H), 6.92 ppm (s, 1H, 3'-H).

Sources & evidence

ORD record: ord-862c1340c5344140902b193d959d30cb
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05677336

Reaction notes

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