4-(1H-imidazol-1-yl)benzaldehyde → (E)-4-[4-(1H-Imidazol-1-yl)phenyl]-3-butenoic acid

HRID 1769656Notes

Reaction equation

[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl-].[C:15]([CH2:18][CH2:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:17])=[O:16].CC(C)([O-])C.[K+]>O1CCCC1>[N:1]1([C:6]2[CH:13]=[CH:12][C:9](/[CH:10]=[CH:19]/[CH2:18][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: -50 °C

Procedure

5.45 g of 4-(1H-imidazol-1-yl)benzaldehyde and 12.93 g of β-carboxyethyltriphenylphosphonium chloride were suspended in 70 ml of tetrahydrofuran. The obtained suspension was cooled to -50° C. and vigorously stirred. 30 ml of a solution of 7.83 g of potassium t-butoxide in tetrahydrofuran was gradually added dropwise to the resulting suspension. The temperature of the obtained mixture was gradually raised to 0° C. After one hour, ice-water was added to the mixture. The obtained mixture was washed with ether. The pH of the aqueous layer was adjusted with concentrated hydrochloric acid to about 4 to precipitate a solid. This solid was recovered by filtration and washed with water and methanol to obtain 5.44 g of the title compound as a pale yellow powder (yield: 75%).

Workup

temperatureThe temperature of the obtained mixture was gradually raised to 0° C
washThe obtained mixture was washed with ether
customto precipitate a solid
filtrationThis solid was recovered by filtration
washwashed with water and methanol

Sources & evidence

ORD record: ord-bba87c176fae411f9fd892cb3c223871
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382595

Reaction notes

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