Tributylphosphine → HCID 86591573, compound

HRID 1294342Notes

Reaction equation

HRID 1294342 reaction equation
[CH3:1][CH:2]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1)[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.O[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:1][CH:2]([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1)[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 86591570HCID 86591570, compound

Product 1

HCID 86591573HCID 86591573, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-[methyl(4-phenyl-2-thiazolyl)aminomethyl]benzyl alcohol (1.00 g), methyl 2-(4-hydroxyphenyl)acetate (643 mg), tributylphosphine (1.30 g) and tetrahydrofuran (30 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.62 g) at room temperature and the mixture was stirred for 16 hrs. The precipitated crystals were filtered off. The filtrate was concentrated and the residue was subjected to silica gel column chromatography to give methyl 4-[4-[methyl(4-phenyl-2-thiazolyl)aminomethyl]benzyloxy]phenylacetate (1.48 g, quantitative) as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. filtrationThe precipitated crystals were filtered off
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0248939543da42b78e24e6daaf260534
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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