Sodium Bicarbonate → Ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate

HRID 1927432Notes

Reaction equation

HRID 1927432 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[C:10](O)=[O:11])[CH3:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][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:23])=[CH:20][CH:19]=1)#[N:22]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 578313802-[2-(4-Cyanophenyl)ethyl]heptanedioic acid 7-ethyl ester

Product 1

HCID 57831363Ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

54.19 ml (54.19 mmol) of a 1 M borane-THF complex solution are added dropwise to a solution of 8.6 g (27.1 mmol) of 2-[2-(4-cyanophenyl)ethyl]heptanedioic acid 7-ethyl ester 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 1:10→1:4). 5.1 g (97%, 60% of theory) 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 1:10→1:4)
  5. custom5.1 g (97%, 60% of theory) of a colorless solid are obtained

Sources & evidence

ORD record
ord-9b80b1d8761e4cc7ac6d74d06c21aa15
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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