Sodium Bicarbonate → Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate

HRID 1927407Notes

Reaction equation

[C:1]([CH:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(O)=[O:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH:4]([CH2:1][OH:2])[CH2:5][CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)=[CH:23][CH:22]=1)#[N:25]

Participants

Conditions

Temperature: -5 °C

Procedure

47.43 ml (47.73 mmol) of a 1 M borane-THF complex solution are added dropwise to a solution of 8 g (23.71 mmol) of methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate in 200 ml of THF at −10° C. After warming to −5° C., the mixture is stirred at this temperature for a further 4 hours. After reaction is complete, the reaction mixture is mixed with saturated sodium bicarbonate solution, 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). 5.8 g (98% purity, 74% of theory) of a colorless solid are obtained.

Workup

customAfter reaction
concentrationthe solvent is concentrated to dryness
dry with materialdried over sodium sulfate
customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10)
custom5.8 g (98% purity, 74% of theory) of a colorless solid are obtained

Sources & evidence

ORD record: ord-c07d5b92ee0e46eab3334de88ce45bf8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183271B2

Reaction notes

Loading…