HCID 18977580, compound → HCID 22904118, compound

HRID 1489205Notes

Reaction equation

HRID 1489205 reaction equation
[H][H].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[C:18](=[O:19])[CH:17]=[CH:16][CH2:15][C:14]2([CH3:21])[CH3:20])=[CH:8][CH:7]=1)([O-:5])=[O:4]>C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH:13]2[C:14]([CH3:20])([CH3:21])[CH2:15][CH2:16][CH2:17][C:18]2=[O:19])=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

5

Reactant 2

HCID 18977580HCID 18977580, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22904118HCID 22904118, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 241BenzeneSolvent

Procedure

An atmosphere of hydrogen was introduced to and maintained by a balloon to an evacuated 50 mL round-bottomed flask containing 6-(4'-nitrophenyl)methyl-5,5-dimethylcyclohex-2-en-1-one (39) (14.0 mg, mmol) and tris(triphenylphosphine)rhodium chloride (Wilkinson's catalyst) (8.0 mg) in 6.5 mL anhydrous benzene. The yellow-orange solution was stirred at room temperature for 24 h, and then passed through a short silica gel column (hexanes/ethyl acetate, 3:1) to afford the 6.8 mg (48%) of the desired ketone as a pale yellow oil (Rf0.43, 2:1 hexanes lethyl acetate). 1H NMR (400MHz, CDCl3) δ0.86 and 1.23 (2s, 2×3H, geminal-CH3 's), 2.50 (d, 1H, J=13.0 Hz, 2-H), 2.66 and 3.17 (d of ABq, 2H, JAB =13.0 Hz, JA =1.6 Hz, JB =9.6 Hz, benzylic-CH2), 7.37 (d, 2H, J=9.6 Hz, 2', 6'-H), 8.09 ppm (d, 2H, J=9.6 Hz, 3',5'-H). [Compound 40 is hereinafter also referred to as COMPOUND "V" or 120211]

Workup

  1. temperaturemaintained by a balloon to an evacuated 50 mL round-bottomed flask

Sources & evidence

ORD record
ord-4fd63605241b4da5a37202ed10f58ba2
Source dataset
uspto-grants-1997_10
Patent number
US05677336

Reaction notes

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