Tributylphosphine → HCID 86615988, compound

HRID 1160922Notes

Reaction equation

HRID 1160922 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[Cl:49][C:50]1[N:55]=[CH:54][C:53](O)=[CH:52][C:51]=1[CH3:57]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:16][C:53]2[CH:54]=[N:55][C:50]([Cl:49])=[C:51]([CH3:57])[CH:52]=2)[CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 128520156-Chloro-5-methylpyridin-3-olHCID 59518034HCID 59518034, compound

Product 1

HCID 86615988HCID 86615988, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(1-hydroxy-3,3-dimethyl-butyl)-benzoic acid methyl ester (450 mg, 1.91 mmol) in toluene (19 mL) is added 1,1′-(azodicarbonyl)dipiperidine (ADDP, 722 mg, 2.86 mmol) at 0° C., followed by the additions of tributylphosphine (0.71 mL, 2.86 mmol) and 6-chloro-5-methyl-pyridin-3-ol (327 mg, 2.29 mmol). The reaction mixture is warmed up to room temperature and stirred overnight. The mixture is loaded on silica gel, eluted with hexanes with a gradient from 0% of ethyl acetate to 50% of ethyl acetate giving the titled compound (440 mg).

Workup

  1. washeluted with hexanes with a gradient from 0% of ethyl acetate to 50% of ethyl acetate giving the titled compound (440 mg)

Sources & evidence

ORD record
ord-c0d1a27af83342eea1df11e761ff9f0e
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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