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

HRID 569488

Reaction equation

HRID 569488 reaction equation
[C:1]([C:9]1[CH:13]=[CH:12][O:11][C:10]=1[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>[Pd]>[CH:1](/[C:9]1[CH:13]=[CH:12][O:11][C:10]=1[CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 1

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

Product 1

HCID 70416255Diethyl 2-[(Z)-3-(1-Octenyl)-2-furanylmethylene]propan-1,3-dioateYield 80.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Diethyl 2-[3-(1-octynyl)-2-furanylmethylene]propan-1,3-dioate(1.04 g, 3 mmole from example 16) was hydrogenated over 5% palladium on barium sulphate as described in Example 12 to yield, after chromatography on silica (DCM:Hexane 1:1) the title compound 0.84 g (80%) as an oil, νmax (film) 1740, 1720, 1610, 1025, 885, 865, 760; δ(CDCl3) 0.88(3H, distorted t), 1.32(3H, t, J=7 Hz), 1.34(8H, m), 1.37(3H, t, H=7 Hz), 2.26(2H, m), 4.28(2H, q, J=7 Hz), 4.40(2H, q, J=7 Hz), 5.8(1H, m), 6.33(1H, m), 6.6(1H, d, J=2 Hz), 7.45(1H, d, J=2 Hz), 7.49(1H, s).

Workup

  1. customto yield

Sources & evidence

ORD record
ord-deb8ecd7a3724fcab368a3ad9ad31a7a
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Linked notes

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