Diisopropyl Ether → HCID 131721646, compound

HRID 377378Notes

Reaction equation

HRID 377378 reaction equation
[CH3:1][O:2][C:3](=[CH:7][CH:8]=[CH:9][C:10]1[S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[C:14]=1[CH3:15])[C:4]([O-:6])=[O:5].[CH2:20]1CCN2C(=NCCC2)CC1.C(OC(C)C)(C)C>C(Cl)Cl>[CH3:1][O:2]/[C:3](=[CH:7]/[CH:8]=[CH:9]/[C:10]1[S:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[C:14]=1[CH3:15])/[C:4]([O:6][CH3:20])=[O:5]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131721647HCID 131721647, compound2×

Product 1

HCID 131721646HCID 131721646, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (2Z,4E)-2-(methoxy-5-(3-methylbenzothiophen-2-yl)-2,4-pentadienoate and methyl (2Z,4E)-2-(methoxy-5-(3-methylbenzothiophen-2-yl)-2,4-pentadienoate. A solution of (E)-3-[2-(3-methylbenzothiophen-2yl)]-2-propenal (1 g, 5 mmol) in CH2Cl2 (30 ml) under nitrogen was treated with methoxycarbonylmethyl-2-methoxy triphenylphosphonium bromide (4.45 g, 10 mmol) and DBU (1.5 ml, 10 mmol). The reaction mixture was stirred at room temperature for 2 hours, washed with 10% aqueous HCl (5 ml), saturated solution of NaHCO3 (5 ml) and brine (5 ml), dried over Na2SO4 and evaporated under vacuum. The residue was purified by chromatography on silicagel (hexane/EtOAc 7/3) to afford, after trituration with isopropyl ether, methyl (2Z,4E)-2-methoxy-5-)3-methylbenzothiophen-2-yl)-2,4-pentiadienoate (380 mg, 1.32 mmol, yield 26.3%), m.p.=106-107° C., and methyl (2E,4E)-2-methoxy-5-(methylbenzothiophen-2-yl)-2,4-pentadienoate, (13 mg, 0.050 mmol, yield 1.0%), m.p.=91-92° C.

Workup

  1. washwashed with 10% aqueous HCl (5 ml), saturated solution of NaHCO3 (5 ml) and brine (5 ml)
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum
  4. customThe residue was purified by chromatography on silicagel (hexane/EtOAc 7/3)
  5. customto afford

Sources & evidence

ORD record
ord-e8c4ab0c8177424586023306554ccd77
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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