Tributylphosphine → HCID 23159930, compound

HRID 2110906Notes

Reaction equation

HRID 2110906 reaction equation
[CH2:1]([O:8][C:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=2)[N:12]=[C:11]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:27][C:28]1[CH:33]=[C:32](O)[CH:31]=[CH:30][C:29]=1[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH2:1]([O:8][C:9]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][O:22][C:32]3[CH:31]=[CH:30][C:29]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:28]([F:27])[CH:33]=3)=[CH:19][CH:20]=2)[N:12]=[C:11]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23082888Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoateHCID 23157444HCID 23157444, compound

Product 1

HCID 23159930HCID 23159930, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (4-([5-(benzyloxy)-3-tert-butyl-1H-pyrazol-1-yl]methyl)phenyl)methanol (0.60 g, 1.7 mmol), ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate (0.40 g, 1.9 mmol), tributylphosphine (0.85 mL, 3.4 mmol) and tetrahydrofuran (50 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.86 g, 3.4 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated under reduced pressure, diisopropyl ether was added to the residue, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to give the title compound (0.82 g, yield 88%) as a colorless oil. MS: m/z 545 (MH+).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, diisopropyl ether
  2. additionwas added to the residue
  3. filtrationthe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bfadc5561b5544d8b76feea7b854d354
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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