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Tributylphosphine → HCID 69589641, compound

HRID 860681
Notes
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Reaction equation

HRID 860681 reaction equation
C(P(CCCC)CCCC)CCC.[CH3:14][O:15][C:16](=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=1.[CH:26]([C:29]1[N:30]=[C:31]([C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=2)[O:32][C:33]=1[CH:34]([CH3:37])[CH2:35]O)([CH3:28])[CH3:27]>C1(C)C=CC=CC=1.CCOCC>[CH3:14][O:15][C:16](=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:37][CH:34]([C:33]2[O:32][C:31]([C:38]3[CH:43]=[CH:42][C:41]([C:44]([F:45])([F:46])[F:47])=[CH:40][CH:39]=3)=[N:30][C:29]=2[CH:26]([CH3:28])[CH3:27])[CH3:35])[CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 13831TributylphosphineHCID 39129Methyl 3-HydroxyphenylacetateHCID 58765710HCID 58765710, compound

Product 1

HCID 69589641HCID 69589641, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283
Diethyl Ether
Solvent

Procedure

Azodicarboxylic dipiperidide (0.31 g, 1.23 mmol) is stirred in 5 mL toluene at −30 to −20 deg C. Tri-n-butyl phosphine (0.31 mL, 1.23 mmol) is added dropwise and the mixture is stirred at −30 to −20 deg C. 10–15 min. An intimate mixture of (3-hydroxy-phenyl)-acetic acid methyl ester (0.13 g, 0.77 mmol) and 2-[4-isopropyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-1-ol (0.20 g, 0.701 mmol) in toluene (5 mL) is added dropwise and the resulting mixture is stirred 18 hr at room temperature. The thick suspension is diluted with 25 mL ether and cooled on ice/water for 30 min. The mixture is filtered, concentrated, and purified via silica gel chromatography eluting with 98:2 hexanes:acetone to afford the title compound as a colorless thick oil, 0.10 g, 31%. MS M++1 462. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. custom10–15 min
  2. additionis added dropwise
  3. stirringthe resulting mixture is stirred 18 hr at room temperature
  4. temperaturecooled on ice/water for 30 min
  5. filtrationThe mixture is filtered
  6. concentrationconcentrated
  7. custompurified via silica gel chromatography
  8. washeluting with 98:2 hexanes

Sources & evidence

ORD record
ord-1037019d0bdd4722b2edd77ba7414f67
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07153878B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes