5-(2-Ethyl-[1,3]dioxolan-2-yl)thiophene-2-carbaldehyde → Dimethyl 4-{(e)-2-[5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienyl]vinyl}phthalate

HRID 49335Notes

Reaction equation

HRID 49335 reaction equation
C(OP([CH2:9][C:10]1[CH:11]=[C:12]([C:20]([O:22][CH3:23])=[O:21])[C:13](=[CH:18][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15])(OCC)=O)C.[CH2:24]([C:26]1([C:31]2[S:35][C:34]([CH:36]=O)=[CH:33][CH:32]=2)[O:30][CH2:29][CH2:28][O:27]1)[CH3:25].CC(C)([O-])C.[K+]>C1COCC1>[CH2:24]([C:26]1([C:31]2[S:35][C:34](/[CH:36]=[CH:9]/[C:10]3[CH:11]=[C:12]([C:20]([O:22][CH3:23])=[O:21])[C:13](=[CH:18][CH:19]=3)[C:14]([O:16][CH3:17])=[O:15])=[CH:33][CH:32]=2)[O:27][CH2:28][CH2:29][O:30]1)[CH3:25]

Participants

5

Reactant 3

HCID 179347875-(2-Ethyl-[1,3]dioxolan-2-yl)thiophene-2-carbaldehydeHCID 22345602HCID 22345602, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20636328Dimethyl 4-{(e)-2-[5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienyl]vinyl}phthalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18.5 g (53.7 mmol) of dimethyl 4-(diethoxyphosphorylmethyl)phthalate and 9.5 g (44.7 mmol) of 5-(2-ethyl-[1,3]dioxolan-2-yl)thiophene-2-carbaldehyde (described in Example 6(b)) are dissolved in 200 mL of anhydrous THF. 6.02 g (53.7 mmol) of potassium tert-butoxide are added and the mixture is stirred for 24 h. After the usual treatment and chromatography on silica gel (eluent: 8 heptane/2 ethyl acetate), the desired product is obtained in the form of a yellow oil (m=9.53 g, Y=53%).

Sources & evidence

ORD record
ord-ce402458bdb24b5a8c0d1939ffcc1b30
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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