4-Hydroxybenzaldehyde → HCID 135725115, compound

HRID 1369947Notes

Reaction equation

HRID 1369947 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[S:17][CH:18]=[C:19]([CH2:21][CH2:22][OH:23])[N:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].O[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:12]([C:9]1[CH:8]=[C:7]([C:16]2[S:17][CH:18]=[C:19]([CH2:21][CH2:22][O:23][C:25]3[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=3)[N:20]=2)[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 135725051HCID 135725051, compound

Product 1

HCID 135725115HCID 135725115, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

The compound of Step E 4.20 g (12.6 mmole), 1.76 g (14.44 mmole) 4-hydroxybenzaldehyde, and 3.79 g (14.44 mmole) triphenyl phosphine were dissolved in 37 ml tetrahydrofuran with stirring, under nitrogen. The solution was chilled to −10° C. and a solution of 2.27 ml (14.44 mmole) diethylazodicarboxylate in 12.5 ml, tetrahydrofuran was added over 10 minutes, with stirring. The reaction exothermed to −1° C. The bath was removed and the reaction stirred under nitrogen overnight. The reaction was stripped, dissolved in methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed on 400 ml silica, eluting with a 15 then 20% ethyl acetate/hexane. The appropriate fractions were bulked and stripped to give 3.98 g (72%) product which was used without further purification.

Workup

  1. stirringwith stirring
  2. customexothermed to −1° C
  3. customThe bath was removed
  4. stirringthe reaction stirred under nitrogen overnight
  5. dissolutiondissolved in methylene chloride
  6. filtrationThe diethoxycarbonylhydrazine was then filtered off
  7. customthe filtrate was chromatographed on 400 ml silica
  8. washeluting with a 15

Sources & evidence

ORD record
ord-62d203ae6c9a412398ceae4bf527d4ee
Source dataset
uspto-grants-2003_06
Patent number
US06579871B2

Reaction notes

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