Sodium Bicarbonate → Ethyl 6-(4-cyanobenzyl)-7-hydroxyheptanoate

HRID 1927441Notes

Reaction equation

HRID 1927441 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=1)[C:10](O)=[O:11])[CH3:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH:9]([CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:22])=[CH:19][CH:18]=1)#[N:21]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 578313612-(4-Cyanobenzyl)heptanedioic acid 7-ethyl ester

Product 1

HCID 22561016Ethyl 6-(4-cyanobenzyl)-7-hydroxyheptanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

34.42 ml of a 1 M borane-THF complex solution (34.42 mmol) are added dropwise to a solution of 6.64 g (22.94 mmol) of 2-(4-cyanobenzyl)heptanedioic acid 7-ethyl ester in 260 ml of THF at −10° C. After warming to 0° C., the mixture is stirred at this temperature for 2 hours. After the 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). 5.84 g (88% of theory, 20.19 mmol) of a colorless solid are obtained.

Workup

  1. concentrationthe solvent is concentrated to dryness
  2. dry with materialdried over sodium sulfate
  3. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:8→1:2)
  4. custom5.84 g (88% of theory, 20.19 mmol) of a colorless solid are obtained

Sources & evidence

ORD record
ord-eaa8ec7b1eb94ef6b22346a6b9387ea0
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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