Piperonal → HCID 67985934, compound

HRID 718537Notes

Reaction equation

[I-].[CH3:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.ICCC1C=CC(C)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Li]CCCC.[O:64]1[C:68]2[CH:69]=[CH:70][C:71]([CH:73]=O)=[CH:72][C:67]=2[O:66][CH2:65]1>>[C:3]1([CH3:2])[CH:4]=[CH:5][C:6]([CH2:7][CH:8]=[CH:73][C:71]2[CH:70]=[CH:69][C:68]3[O:64][CH2:65][O:66][C:67]=3[CH:72]=2)=[CH:28][CH:29]=1

Participants

Reactant 5

HCID 8438Piperonal

HCID 11776Triphenylphosphine

HCID 184025521-(2-Iodoethyl)-4-methylbenzene

HCID 86702778HCID 86702778, compound

HCID 178418339Butyllithium

Product 1

HCID 67985934HCID 67985934, compoundYield 40%

Procedure

Starting from p-methylphenethyltriphenylphosphonium iodide, which has been synthesized from 1-(2-iodoethyl)-4-methylbenzene and PPh3, (2.54 g, 5.00 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.1 mL, 5.00 mmol, 1.0 equiv.) and benzo[d][1,3]dioxole-5-carbaldehyde (0.98 g, 6.50 mmol, 1.3 equiv.), 0.50 g (40%) of the title compound as a light yellow oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).

Sources & evidence

ORD record: ord-02e3bdcb9beb4fd59f3c1abac6c2f43f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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