Diethyl Malonate → Diethyl 2-[3-(1-octynyl)-2-furanylmethylene]propan-1,3-dioate

HRID 569487

Reaction equation

HRID 569487 reaction equation
[C:1]([C:9]1[CH:13]=[CH:12][O:11][C:10]=1[CH:14]=O)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:16]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[C:1]([C:9]1[CH:13]=[CH:12][O:11][C:10]=1[CH:14]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]([O:24][CH2:25][CH3:26])=[O:23])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 7761Diethyl MalonateHCID 201471613-(1-Octynyl)furan-2-carboxaldehyde

Product 1

HCID 20147165Diethyl 2-[3-(1-octynyl)-2-furanylmethylene]propan-1,3-dioate

Procedure

Reaction of 3-(1-octynyl)furan-2-carboxaldehyde (2.04 g, 10 mmole from Example 14) with diethyl malonate (1.98 g, 1.25 eq) as described in Example 3 gave, after chromatography on silica (DCM:Hexane 1:1) 1.96 (57%) of the title compound as an oil, νmax (film) 2930, 2230, 1740, 1725, 1625, 1240, 1210, 1100 cm-1 ; δ(CDCl3) 0.89(3H, distorted t), 1.32(3H, t, J=7.5 Hz), 1.35(3H, t, J=7.5 Hz), 1.40(8H, m), 2.40(2H, t, J=6.5 Hz), 4.28(2H, q, J=7.5 Hz), 4.36(2H, q, J=7.5 Hz), 6.45(1H, d, J=2 Hz), 7.40(1H, d, J=2 Hz), 7.60(1H, s).

Workup

  1. customgave

Sources & evidence

ORD record
ord-6bf5bb71b9564267aaed5a9f588f0ea4
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Linked notes

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