Tributylphosphine → HCID 67488067, compound

HRID 2363212Notes

Reaction equation

HRID 2363212 reaction equation
[OH:1][CH:2]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)[CH2:3][CH:4]([CH3:6])[CH3:5].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[C:48]([C:52]1[CH:57]=[CH:56][C:55]([C:58]2[C:63]([CH3:64])=[CH:62][C:61](O)=[CH:60][C:59]=2[CH3:66])=[CH:54][CH:53]=1)([CH3:51])([CH3:50])[CH3:49]>C1COCC1.C1(C)C=CC=CC=1>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:9]=[CH:8][C:7]([CH:2]([O:1][C:61]2[CH:62]=[C:63]([CH3:64])[C:58]([C:55]3[CH:56]=[CH:57][C:52]([C:48]([CH3:50])([CH3:49])[CH3:51])=[CH:53][CH:54]=3)=[C:59]([CH3:66])[CH:60]=2)[CH2:3][CH:4]([CH3:6])[CH3:5])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 533020184'-Tert-butyl-2,6-dimethylbiphenyl-4-OLHCID 59518172Methyl 4-(1-hydroxy-3-methylbutyl)benzoate

Product 1

HCID 67488067HCID 67488067, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Methyl 4-(1-hydroxy-3-methylbutyl)benzoate, Isomer 1 (Preparation 4) (2.00 g, 9.01 mmol) is stirred in THF/toluene and 1,1′-(azodicarbonyl)dipiperidine (ADDP) (3.41 g, 13.51 mmol) at a temperature of 0-5° C., followed by addition of tri-n-butylphosphine (3.36 mL, 13.51 mmol) and 4′-tert-butyl-2,6-dimethylbiphenyl-4-ol (Preparation 2) (2.75, 10.81 mmol). The reaction is allowed to warm to room temperature with stirring for 24 to 48 h. The reaction is loaded on silica gel, and eluted with hexanes using a gradient of 0-100% ethyl acetate to obtain 2.90 g (70%) of product. 1H NMR.

Workup

  1. washeluted with hexanes using a gradient of 0-100% ethyl acetate

Sources & evidence

ORD record
ord-a2f4d52b1e084b95b63e25a1baf5d6a3
Source dataset
uspto-grants-2014_04
Patent number
US08691856B2

Reaction notes

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