Water → HCID 24751629, compound

HRID 922076Notes

Reaction equation

C[O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][CH2:19][CH2:20][OH:21].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].O.CCOC(C)=O>C(C#N)(C)=O.O>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17]/[C:16](/[CH3:22])=[CH:15]/[CH2:14][C:4]1[C:3](=[O:2])[C:8]([CH3:9])=[C:7]([CH3:10])[C:6](=[O:11])[C:5]=1[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

(E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-en-1-ol (29.7 mg, 0.097 mmol) in AcCN (0.5 mL) with 2 drops of H2O was cooled to 0° C. CAN (114.7 mg, 0.209 mmol) was dissolved into AcCN (0.2 mL) and H2O (0.5 mL) and added to a stirred solution of alcohol at 0° C. The reaction was stirred at 0° C. for 1 h and H2O (2 mL) and EtOAc (2 mL) was added, the layers separated and the aqueous phase extracted 3×2 mL EtOAc. The combined organics were washed 2×2 mL saturated brine, dried over anhydrous Na2SO4 and concentrated to a yellow oil. Flash chromatography yielded (E)-2-(7-hydroxy-3-methylhept-2-enyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione (2.2 mg) as a yellow oil (8.2%). 13C NMR (100 MHz, CDCl3) δ 187.9, 187.0, 143.1, 140.4, 104.3, 134.0, 119.7, 77.2, 62.9, 39.3, 32.3, 25.6, 24.0, 16.2, 12.4, 12.3, 12.2

Workup

customthe layers separated
extractionthe aqueous phase extracted 3×2 mL EtOAc
washThe combined organics were washed 2×2 mL saturated brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated to a yellow oil

Sources & evidence

ORD record: ord-a0d562ad7ad44516919026f948cd636d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278085B2

Reaction notes

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