Triethylamine → HCID 21520609, compound

HRID 1282920Notes

Reaction equation

[Cl:1][C:2]1([Cl:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7](Cl)=[O:8].[O:11]([C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[CH:21]([OH:24])[C:22]#[N:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1([Cl:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7]([O:24][CH:21]([C:22]#[N:23])[C:20]1[CH:25]=[CH:26][CH:27]=[C:18]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:19]=1)=[O:8]

Participants

Conditions

Temperature: 10 °C

Procedure

2,2-Dichloro-3,3-dimethylcyclopropanoyl chloride (2.69g) was dissolved in dry toluene (50ml) and this solution was added dropwise to a stirred solution of 3-phenoxymandelonitrile (3.0g) and triethylamine (2.69g) in dry toluene (50ml) maintained at 10°C. The mixture was then stirred at room temperature for 16 hours. The mixture was filtered and the filtrate was washed in turn with 5 % sulphuric acid, saturated sodium bicarbonate and water, and then dried (Na2SO4). The solvent was removed under reduced pressure and the residue purified by chromatography on silica gel eluting in turn with toluene, 1 : 1 toluene/hexane and toluene. The required product was obtained as an oil nD20 1.5630.

Workup

filtrationThe mixture was filtered
washthe filtrate was washed in turn with 5 % sulphuric acid, saturated sodium bicarbonate and water
dry with materialdried (Na2SO4)
customThe solvent was removed under reduced pressure
customthe residue purified by chromatography on silica gel eluting in turn with toluene, 1 : 1 toluene/hexane and toluene

Sources & evidence

ORD record: ord-e885c7cb2faf4b85a88561a2cc9b20da
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03973035

Reaction notes

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