Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl trans-3-[3-(1-Dodecynyl)phenyl]-2-propenoate

HRID 375926Notes

Reaction equation

[C:1]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:21]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[C:1]([C:13]1[CH:14]=[C:15](/[CH:16]=[CH:26]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:18]=[CH:19][CH:20]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(1-dodecynyl)benzaldehyde (23.0 g) in toluene (150 ml) was added carbethoxymethylenetriphenylphosphorane (35.5 g) in one portion. The mixture was warmed at 80° C. for 5 hr, allowed to cool to room temperature, and concentrated in vacuo. The residue was flash chromatographed over silica gel (eluted with ethyl acetate/hexane/1:15). The appropriate fractions were collected and evaporated to afford 21.1 g (73%) of product.

Workup

temperatureto cool to room temperature
concentrationconcentrated in vacuo
customchromatographed over silica gel (eluted with ethyl acetate/hexane/1:15)
customThe appropriate fractions were collected
customevaporated

Sources & evidence

ORD record: ord-62643dc5b30144299fa1423cd581e607
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488061

Reaction notes

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