Diethyl Ether → HCID 19917051, compound

HRID 1464766Notes

Reaction equation

HRID 1464766 reaction equation
[Br-].[S:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH:30]=[CH:31][CH:32]=2)[CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:3]1.[H-].[Na+].C(OCC)C.[Cl:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]=O>CN(C)C=O>[Cl:40][CH2:41][CH2:42][CH2:43][CH2:44]/[CH:45]=[CH:10]/[C:9]1[CH:8]=[C:7]([C:4]2[CH:5]=[CH:6][S:2][CH:3]=2)[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 6430485-chloropentanalHCID 85621417HCID 85621417, compound

Product 1

HCID 19917051HCID 19917051, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

400 mg of 3-(3-thienyl)benzyl(triphenyl)phosphonium bromide was dissolved in 2 ml of dimethylformamide, and under ice cooling, 37 mg of 60% oily sodium hydride was added. The mixture was stirred for 15 minutes, and to this solution was added an ethyl ether solution (0.6 ml) of the foregoing aldehyde compound. The mixture was stirred overnight at room temperature, and then the solvent was evaporated. The residue was worked up in a customary manner, and purified by silica gel column chromatography [hexane/ethyl acetate=19/1] to give 123 mg of the captioned compound (a mixture of E:Z=1:1) as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customthe solvent was evaporated
  3. custompurified by silica gel column chromatography [hexane/ethyl acetate=19/1]

Sources & evidence

ORD record
ord-1d3a0768b5f04a8fa269f4bcc27abcde
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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