Diisopropylamine → HCID 21189726, compound

HRID 1068572Notes

Reaction equation

HRID 1068572 reaction equation
[CH:1]([NH:4]C(C)C)(C)[CH3:2].C([Li])CCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:18]=[O:19].[Cl-].[NH4+]>O1CCCC1.C(#N)C.CCCCCC>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]([OH:19])[CH2:2][C:1]#[N:4])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 8419VeratraldehydeHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 21189726HCID 21189726, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of diisopropylamine (0.67 g, 6.62 mM) in dried tetrahydrofuran (5 ml) was cooled to −78° C. A hexane solution of n-butyllithium (6.62 mM) was dropped into this solution, then this was stirred at that temperature for 30 minutes. Next, acetonitrile (0.27 g, 6.62 mM) was dropped into this solution and the result stirred for a further 30 minutes, then a solution of 3,4-dimethoxybenzaldehyde (1.00 g, 6.02 mM) in dried tetrahydrofuran (5 ml) was added and the mixture stirred at that temperature for 4 hours. An aqueous ammonium chloride was poured into the obtained solution, which was warmed to room temperature and extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was removed in vacuo to obtain a crude product (1.25 g) of 3-(3,4-dimethoxyphenyl)-3-hydroxypropiononitrile as a yellow oil. The crude product thus obtained had sufficient purity without purification, therefore could be used for the next reaction as it was.

Workup

  1. stirringthe result stirred for a further 30 minutes
  2. stirringthe mixture stirred at that temperature for 4 hours
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto obtain a crude product (1.25 g) of 3-(3,4-dimethoxyphenyl)-3-hydroxypropiononitrile as a yellow oil

Sources & evidence

ORD record
ord-36e70c662bd74b1b807e2f2ac119143e
Source dataset
uspto-grants-2001_06
Patent number
US06251897B1

Reaction notes

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