Tetrahydrofuran → HCID 178471528, compound

HRID 1975616Notes

Reaction equation

HRID 1975616 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:16].[K+].[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11](/[CH:14]=[CH:20]/[C:19]([O:18][CH2:22][CH3:21])=[O:16])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 190979014-(4-Bromophenyl)cyclohexane-1-carbaldehyde

Product 1

HCID 178471528HCID 178471528, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.1 g of 4-(4-bromophenyl)cyclohexanecarb-oxaldehyde and 3.8 g of powdered potassium hydroxide in 200 ml of tetrahydrofuran was placed at room temperature in a sulphonation flask while gassing with argon and treated with 9.2 g of triethyl phosphonoacetate within 15 minutes, stirred overnight, taken up in 100 ml of water and extracted three times with 100 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromato-graphy of the residue (12 g) on silica gel with hexane/ethyl acetate (vol. 9:1) gave 11.7 g of ethyl (E)-3-[trans-4-(4-bromo-phenyl)cyclohexyl]acrylate as colourless crystals.

Workup

  1. customwas placed at room temperature in a sulphonation flask
  2. extractionextracted three times with 100 ml of methylene chloride each time
  3. washThe organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-088a694ada344cf3aeb140b8ff18f938
Source dataset
uspto-grants-1994_02
Patent number
US05288428

Reaction notes

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