Ammonium Chloride → Methyl 4-[4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-(hydroxymethyl)butyl]benzoate

HRID 1920583Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1([CH2:9][CH2:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=2)[C:12](O)=[O:13])[CH2:8][CH2:7]1)[CH3:2].[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1([CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

At −10° C., 12.31 ml of a 1 M borane/THF complex solution (12.31 mmol) are added dropwise to a solution of 2.23 g (6.15 mmol) of 4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-[4-(methoxy-carbonyl)benzyl]butanoic acid in 50 ml of THF. After warming to 0° C., the mixture is stirred at this temperature for another 2 hours and then at room temperature for 1 hour. After complete conversion, saturated ammonium chloride solution is added, and the reaction mixture is extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are then dried over sodium sulfate, and the solvent is evaporated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1). This gives 1680 mg (78% of theory) of a colorless oil.

Workup

waitat room temperature for 1 hour
extractionthe reaction mixture is extracted three times with in each case 50 ml of ethyl acetate
dry with materialThe combined organic phases are then dried over sodium sulfate
customthe solvent is evaporated to dryness

Sources & evidence

ORD record: ord-9807b227d62f43279067a151cd96aa31
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168821B2

Reaction notes

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