Sodium Chloride → HCID 86612572, compound

HRID 1443605Notes

Reaction equation

[C:1]([C:3]([C:22]#[N:23])([CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([C:11](OCC)=[O:12])[CH2:6]1)#[N:2].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[Na+]>O1CCCC1.CCCCCC>[CH:11]([C@@H:7]1[CH2:8][CH2:9][CH2:10][C@H:5]([CH2:4][C:3]([CH2:16][CH2:17][C:18]([F:19])([F:20])[F:21])([C:1]#[N:2])[C:22]#[N:23])[CH2:6]1)=[O:12].[OH:12][CH2:11][C@@H:7]1[CH2:8][CH2:9][CH2:10][C@H:5]([CH2:4][C:3]([CH2:16][CH2:17][C:18]([F:19])([F:20])[F:21])([C:1]#[N:2])[C:22]#[N:23])[CH2:6]1

Participants

Conditions

Temperature: -78 °C

Procedure

Under nitrogen atmosphere, 1.1 g of ethyl cis-3-(2,2-dicyano-5,5,5-trifluoropentyl)cyclohexanecarboxylate was dissolved in 10 ml of tetrahydrofuran. Thereto 7.0 ml of a solution (0.93 mol/L) of diisobutylaluminum hydride in hexane was added dropwise at −78° C. and the mixture was stirred at −78° C. for 2 hours. The reaction mixture was poured into aqueous saturated sodium chloride and then extracted with t-butyl methyl ether. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.18 g of cis-2-(3-formylcyclohexylmethyl)-2-(3,3,3-trifluoropropyl)malononitrile and 0.32 g of cis-2-(3-hydroxymethylcyclohexylmethyl)-2-(3,3,3-trifluoropropyl)malononitrile.

Workup

extractionextracted with t-butyl methyl ether
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7a6d4a4b07d743a0b9ed1d3572bfa14c
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662402B2

Reaction notes

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