Cornforth reagent → HCID 68840242, compound

HRID 2110572Notes

Reaction equation

HRID 2110572 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][C:5]1([C:17]([O:19][CH3:20])=[O:18])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]=[C:6]1[O:15][CH3:16].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:24].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OO)(C)(C)C.O>C1C=CC=CC=1>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][C:5]1([C:17]([O:19][CH3:20])=[O:18])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:24])[CH:7]=[C:6]1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 2724130Cornforth reagentHCID 68838179HCID 68838179, compoundHCID 129889604HCID 129889604, compound

Product 1

HCID 68840242HCID 68840242, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of Example 8A (0.45g, 1.48 mmol), pyridinium dichromate (2.4 g, 5.92 mmol), celite (0.53 g), 70% t-BuOOH/water (0.82 mL, 5.92 mmol) in benzene (11 mL) was stirred at 25° C. for 2 h. The benzene layer was separated and the mixture was extracted with ethyl acetate. The combined organic layers were concentrated in vacuo. Column chromatography on silica (5%→15% ethyl acetate/hexane) afforded the title compound (0.32 g, 67%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.17-0.41 (m, 1H), 0.60-0.81 (m, 10H), 2.16-2.36 (m, 2H), 3.56 (s, 3H), 3.84 (s, 3H), 6.04 (s, 1H), 7.41 (d, J=7.72 Hz, 1H), 7.51 (t, J=6.99 Hz, 1H), 7.60-7.75 (m, 1H), 7.89-8.09 (m, 1H)); MS (ESI) m/z 316.9 (M+H)+.

Workup

  1. customThe benzene layer was separated
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-ed66be1523da45948811116453ba619f
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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