Sodium Bicarbonate → Methyl 4-(6-cyano-2-hydroxymethylhexyl)benzoate

HRID 1672700Notes

Reaction equation

HRID 1672700 reaction equation
[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[N:21])[CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)(O)=[O:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH:4]([CH2:1][OH:2])[CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)#[N:21]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 57864409Methyl 4-(2-carboxy-6-cyanohexyl)benzoate

Product 1

HCID 57864355Methyl 4-(6-cyano-2-hydroxymethylhexyl)benzoateYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

27.65 ml of a 1 M borane-THF complex solution are added dropwise to a solution of 3.835 g (13.83 mmol) of methyl 4-(2-carboxy-6-cyanohexyl)benzoate from Example 116A in 200 ml of THF at −10° C. After warming to 0° C., the mixture is stirred at this temperature for 2 hours. After reaction is complete, saturated sodium bicarbonate solution is added to the reaction mixture, and the solvent is concentrated to dryness. The residue is taken up in dichloromethane, dried over sodium sulfate and again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:8→1:2). 2.95 g (77% yield) of a colorless solid are obtained.

Workup

  1. customAfter reaction
  2. concentrationthe solvent is concentrated to dryness
  3. dry with materialdried over sodium sulfate
  4. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:8→1:2)

Sources & evidence

ORD record
ord-1dacb3d3661a4c24b71039cbe482bd99
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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