3-Cyclopentyloxy-4-methoxybenzaldehyde → trans-1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(2,6-dichlorophenyl)ethene

HRID 1383488Notes

Reaction equation

HRID 1383488 reaction equation
[Br-].[Cl:2][C:3]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:4]=1[CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH:36]1([O:41][C:42]2[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=2[O:50][CH3:51])[CH:45]=O)[CH2:40][CH2:39][CH2:38][CH2:37]1>O1CCCC1>[CH:36]1([O:41][C:42]2[CH:43]=[C:44](/[CH:45]=[CH:5]/[C:4]3[C:25]([Cl:29])=[CH:26][CH:27]=[CH:28][C:3]=3[Cl:2])[CH:47]=[CH:48][C:49]=2[O:50][CH3:51])[CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

5

Reactant 3

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 118435512,6-Dichlorobenzyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22145793trans-1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(2,6-dichlorophenyl)etheneYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A stirred suspension of 2,6-dichlorobenzyltriphenylphosphonium bromide (2.5 g) in dry tetrahydrofuran (30 mL) is treated dropwise with a solution of potassium t-butoxide (0.56 g) in dry tetrahydrofuran (32 mL) at 0° C. After stirring at this temperature for 1 hour, it is treated with a solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (1.1 g) in dry tetrahydrofuran (15 mL). The reaction mixture is stirred from 0° C. to 5° C. for 1 hour and 30 minutes, and then allowed to warm to room temperature. After stirring overnight, the mixture is concentrated and the resulting residue is treated with ethyl acetate (200 mL). The resulting organic solution is filtered. The filtrate is concentrated and the resulting residue is subjected to flash chromatography, eluting with dichloromethane, to give trans-1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(2,6-dichlorophenyl)ethene (1.16 g), m.p. 47-49° C. [Elemental analysis: C,66.4; H,5.6; Cl,19.4%, calculated: C,66.1; H,5.55; Cl,19.5%].

Workup

  1. stirringThe reaction mixture is stirred from 0° C. to 5° C. for 1 hour and 30 minutes
  2. stirringAfter stirring overnight
  3. concentrationthe mixture is concentrated
  4. additionthe resulting residue is treated with ethyl acetate (200 mL)
  5. filtrationThe resulting organic solution is filtered
  6. concentrationThe filtrate is concentrated
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-0c6c10ecf3144cd3bec0e50fb3987d0d
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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