Tributylphosphine → HCID 23159874, compound

HRID 2110878Notes

Reaction equation

HRID 2110878 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[CH:14][CH:15]=2)=[CH:2]1.O[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[CH2:16][O:17][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)=[CH:2]1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 23111775HCID 23111775, compound

Product 1

HCID 23159874HCID 23159874, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(1-benzothiophen-3-yl)phenyl]methanol (0.70 g, 2.91 mmol), methyl 3-(4-hydroxyphenyl)propanoate (0.58 g, 3.22 mmol) and tributylphosphine (0.95 mL, 3.81 mmol) in anhydrous tetrahydrofuran (40 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.96 g, 3.80 mmol) by small portions, and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with diethyl ether (40 mL). The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:5) to give the title compound (1.0 g, yield 85%) as a colorless oil. MS: m/z 403 (MH+).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc15272a408341a09279af5757abf1d4
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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