4-Hydroxy-3,5-bis(isopropyl)benzaldehyde → HCID 9905645, compound

HRID 1351454Notes

Reaction equation

HRID 1351454 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])[CH:7]=O)([CH3:3])[CH3:2].[S:16]([CH2:22][C:23]#[N:24])([CH2:19][C:20]#[N:21])(=[O:18])=[O:17]>C(O)C.N1CCCCC1>[C:20]([CH2:19][S:16](/[C:22](=[CH:7]/[C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:11]([OH:12])=[C:10]([CH:13]([CH3:15])[CH3:14])[CH:9]=1)/[C:23]#[N:24])(=[O:18])=[O:17])#[N:21]

Participants

5

Reactant 2

HCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeHCID 142163Sulphonyl diacetonitrile

Product 1

HCID 9905645HCID 9905645, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 500 mg of 3,5-diisopropyl-4-hydroxybenzaldehyde and 700 mg of sulfonyl diacetonitrile in 6 ml of ethanol was refluxed with a few drops of piperidine for 4 hours. Ethanol was removed in a rotavap and the mixture worked up with ethyl acetate, diluted acid and brine. A portion of the crude was then purified by HPLC on a C-18 column to provide 50 mg of M27 along with 30 mg of M29.

Workup

  1. customEthanol was removed in a rotavap
  2. additiondiluted acid and brine
  3. customA portion of the crude was then purified by HPLC on a C-18 column
  4. customto provide 50 mg of M27 along with 30 mg of M29

Sources & evidence

ORD record
ord-a7df700bae45437a95ba71552b35804a
Source dataset
uspto-grants-2007_05
Patent number
US07217737B2

Reaction notes

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