4-Hydroxybenzaldehyde → HCID 86598289, compound

HRID 902664Notes

Reaction equation

HRID 902664 reaction equation
[Cl:1][C:2]([N:13]([CH2:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14][CH2:15][CH2:16][OH:17])([C:9]([F:12])([F:11])[F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O[C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]([N:13]([CH2:18][CH:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:14][CH2:15][CH2:16][O:17][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=1)([C:9]([F:11])([F:12])[F:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 69253642HCID 69253642, compound

Product 1

HCID 86598289HCID 86598289, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-[(Chloro-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol (0.500 g, 1.12 mmol) in toluene (4 ml) at ambient temperature was added 4-Hydroxy-benzaldehyde (0.213 g, 1.74 mmol) under Argon with stirring. The mixture was treated with polymer bound PPh3 (0.594 g, 1.782 mmol). After 15 minutes of stirring, the mixture was treated with DIAD (0.273 mL, 1.387 mmol) and was stirred at ambient temperature overnight. The reaction mixture was filtered then concentrated, in-vacuo, to dryness. The oil was dissolved in DMSO and was purified via reverse-phase HPLC to yield the title compound (0.266 g, 43%); MS (ES+) m/e 553 [M+H]+.

Workup

  1. additionThe mixture was treated with polymer
  2. stirringAfter 15 minutes of stirring
  3. stirringwas stirred at ambient temperature overnight
  4. filtrationThe reaction mixture was filtered
  5. concentrationthen concentrated
  6. dissolutionThe oil was dissolved in DMSO
  7. customwas purified via reverse-phase HPLC

Sources & evidence

ORD record
ord-03668f0fae41475c8f9f260cd618a301
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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