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

HRID 1092821Notes

Reaction equation

HRID 1092821 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 1.5 hours, 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 1.5 hours
  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-173be4f0b2004f7588076d169129eae3
Source dataset
uspto-grants-2012_03
Patent number
US08129537B2

Reaction notes

Loading…