2-(Trimethylsilyl)ethanethiol → 3-Cyano-1-(furan-3-yl)-6-[2-trimethylsilylethylthio]naphthalene

HRID 741835Notes

Reaction equation

HRID 741835 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[CH:18]=[CH:17][O:16][CH:15]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9](I)=[CH:8][CH:7]=2)#[N:2].[CH3:19][Si:20]([CH3:25])([CH3:24])[CH2:21][CH2:22][SH:23].CC(C)([O-])C.[K+]>CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[CH:18]=[CH:17][O:16][CH:15]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([S:23][CH2:22][CH2:21][Si:20]([CH3:25])([CH3:24])[CH3:19])=[CH:8][CH:7]=2)#[N:2]

Participants

6

Reactant 3

HCID 2055212-(Trimethylsilyl)ethanethiolHCID 233702222-Cyano-4-(3-furyl)-7-iodonaphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 194269713-Cyano-1-(furan-3-yl)-6-[2-trimethylsilylethylthio]naphthaleneYield 70.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-cyano-1-(furan-3-yl)-6-iodonaphthalene (2.5 g, 7.25 mmol), 2-(trimethylsilyl)ethanethiol (974 mg, 7.25 mmol), potassium tert-butoxide (1.624 g, 14.5 mmol) and (Ph3P)4Pd (200 mg, 0.17 mmol) in EtOH (250 mL) was refluxed for 6.5 h. After evaporation of the EtOH, the residue was partitioned between Et2O and H2O. The crude product from the organic phase was chromatographed on silica gel, eluting with a 1:9 mixture of EtOAc and hexane to afford the title product (1.8 g) as an amber oil.

Workup

  1. temperaturewas refluxed for 6.5 h
  2. customAfter evaporation of the EtOH
  3. customthe residue was partitioned between Et2O and H2O
  4. customThe crude product from the organic phase was chromatographed on silica gel
  5. washeluting with a 1:9 mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-12bc4385c80a4ea0989c0e8be00cd388
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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