Water → HCID 20077560, compound

HRID 1655082Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[CH:5][C:4]=1[OH:11])#[N:2].[H-].[Na+].Br[C:15]([CH3:19])([CH3:18])[CH:16]=[O:17].O>CN1C(=O)N(C)CCC1>[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[CH:5][C:4]=1[O:11][C:15]([CH3:19])([CH3:18])[CH:16]=[O:17])#[N:2]

Participants

Conditions

Temperature: 4 °C

Procedure

2-Cyano-4-ethylphenol (1.47 g) was added portionwise to a stirred, ice-cooled suspension of sodium hydride (60% w/w dispersion in mineral oil, 420 mg) in DMPU (10 ml) under argon. Stirring was continued for 1 hour at ambient temperature, the mixture cooled to 4° C. and 2-bromo-2-methylpropanal (2.26 g) in DMPU (2 ml) added. Stirring was continued for 18 hours at ambient temperature. Water (50 ml) was added and the resulting mixture extracted with ether (3×50 ml). The combined extracts were washed with water (2×30 ml) and saturated brine (2×30 ml), then dried (MgSO4). Evaporation of the solvent and purification of the residual oil by flash chromatography, eluting with 20% v/v ethyl acetate in hexane, gave 2-(2-cyano-4-ethylphenoxy)-2-methylpropanal (2.04 g), as a colourless oil;

Workup

temperaturecooled
stirringStirring
waitwas continued for 18 hours at ambient temperature
extractionthe resulting mixture extracted with ether (3×50 ml)
washThe combined extracts were washed with water (2×30 ml) and saturated brine (2×30 ml)
dry with materialdried (MgSO4)
customEvaporation of the solvent and purification of the residual oil by flash chromatography
washeluting with 20% v/v ethyl acetate in hexane

Sources & evidence

ORD record: ord-c083f42c30ff4ef696fbadd3295a3c27
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05410064

Reaction notes

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