Tributylstannane → Acetate

HRID 2229979Notes

Reaction equation

HRID 2229979 reaction equation
C([SnH](CCCC)CCCC)CCC.Br[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[OH:21].[C:22]([O:30][CH:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[N:34]([OH:39])[C:33]([CH3:41])([CH3:40])[CH2:32]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCCCCCC>ClC1C=CC=CC=1>[C:22]([O-:30])(=[O:29])[CH3:23].[C:22]([O:30][CH:31]1[CH2:32][C:33]([CH3:40])([CH3:41])[N:34]([O:39][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[OH:21])[C:35]([CH3:38])([CH3:37])[CH2:36]1)(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 5948TributylstannaneHCID 8900HeptaneHCID 2664112-BromocyclohexanolHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 2

HCID 175AcetateHCID 225076454-Benzoyloxy-1-(2-hydroxycyclohexyloxy)-2,2,6,6-tetramethylpiperidine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Tributyltin hydride is added dropwise to a solution of 2-bromocyclohexanol and excess 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine in chlorobenzene. The mixture is heated to facilitate reaction. The crude reaction mixture is passed through silica gel with heptane and then heptanelethyl acetate to afford the title compound as a mixture os cis/trans isomers.

Workup

  1. temperatureThe mixture is heated
  2. customreaction
  3. customThe crude reaction mixture

Sources & evidence

ORD record
ord-6aa6917e249f4f8ab932d7fb6c760d93
Source dataset
uspto-grants-2002_07
Patent number
US06420562B2

Reaction notes

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