1,1,3,3-Tetramethylguanidine → (Z)-3-(1H-indol-5-yl)-2-methoxy-acrylic Acid Benzyl Ester

HRID 2181184Notes

Reaction equation

HRID 2181184 reaction equation
[Cl-].[CH3:2][O:3][CH:4]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C(=N)N(C)C.[CH:42]([C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][CH:48]=[CH:47]2)=O>ClCCl>[CH2:7]([O:6][C:5](=[O:14])/[C:4](/[O:3][CH3:2])=[CH:42]/[C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][CH:48]=[CH:47]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 664601,1,3,3-Tetramethylguanidine2×HCID 589040Indole-5-carboxaldehydeHCID 18003490(Benzyloxycarbonyl-methoxy-methyl)-triphenyl-phosphonium chloride

Product 1

HCID 69563356(Z)-3-(1H-indol-5-yl)-2-methoxy-acrylic Acid Benzyl EsterYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.70 g of (1-methoxy-2-benzyloxy-oxoethyl)triphenyl phosphonium chloride in 60 ml of dichloromethane was added at 0° C. 1.07 ml of tetramethyl guanidine and the mixture was warmed to 22° C. The mixture was treated with 2.25 g of 5-formyl-indole and stirring was continued at 40° C. for 16 h. The mixture was treated again with 3.70 g of the Wittig salt and 1.07 ml of tetramethyl guanidine and stirring was continued at 40° for 24 h after which time the conversion was complete. The mixture was evaporated and the residue partitioned between AcOEt and water. The organic layer was dried, evaporated and the residue chromatographed on silica (n-hexane/AcOEt, 4:1) to give 1.67 g of the title compound as a pale yellow oil. MS: (M+H)+ 308.2.

Workup

  1. stirringstirring
  2. waitwas continued at 40° for 24 h
  3. customThe mixture was evaporated
  4. customthe residue partitioned between AcOEt and water
  5. customThe organic layer was dried
  6. customevaporated
  7. customthe residue chromatographed on silica (n-hexane/AcOEt, 4:1)

Sources & evidence

ORD record
ord-071c3d8eeaf0428693bce329c87eaaf9
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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