Water → 2-(5-Hydroxypentyl)-2-(3,3,3-trifluoropropyl)malononitrile

HRID 1443596Notes

Reaction equation

C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH2:19][CH2:20][C:21]([F:24])([F:23])[F:22])([C:17]#[N:18])[C:15]#[N:16])C1C=CC=CC=1.[I-].[Na+].O>C(#N)C>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH2:19][CH2:20][C:21]([F:22])([F:23])[F:24])([C:17]#[N:18])[C:15]#[N:16]

Participants

Conditions

Temperature: 0 °C

Procedure

1.8 g of 2-(5-benzyloxypentyl)-2-(3,3,3-trifluoropropyl)malononitrile was added to 20 ml of acetonitrile was cooled to 0° C. To the mixture, 1.6 g of sodium iodide added and 1.3 g of trifluoroborane-diethyl ether complex dissolved in 5 ml of acetonitrile was further added dropwise. The mixture was stirred at 0° C. for 1 hour and at room temperature for 6 hours. Thereafter, water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed successively with water and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.40 g of 2-(5-hydroxypentyl)-2-(3,3,3-trifluoropropyl)malononitrile.

Workup

additionwas further added dropwise
extractionfollowed by extraction with chloroform
washThe organic layer was washed successively with water and aqueous saturated sodium chloride
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3390515b4e0d4eab89b8c9ec9e4300b7
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662402B2

Reaction notes

Loading…