Methanol → HCID 13645760, compound

HRID 1982201Notes

Reaction equation

HRID 1982201 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:18][CH:19]=[CH2:20])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2].CO.[Br:23]Br.C[O-].[Na+]>C1COCC1.O>[CH2:1]([O:3][C:4]([C:6]1([CH2:18][CH2:19][CH2:20][Br:23])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 24408BromineHCID 10942334Sodium MethoxideHCID 13645759HCID 13645759, compound

Product 1

HCID 13645760HCID 13645760, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The 2-phenyl-1-(2-propenyl)-cyclohexanecarboxylic acid ethyl ester (4.08 g, 15 mmol) was dissolved in THF (10 ml) and cooled to 0°, under nitrogen. Upon addition of 5.2 ml of 1M BH3 -THF, the solution was stirred at 0° for 30 min. then at RT for 30 min. The flask was cooled to 0° and 0.5 ml MeOH was added to destroy any excess hydride. Bromine (1 ml, 20 mmol) was added dropwise followed by the addition of 30 mmol of freshly prepared NaOMe (0.7 g Na metal/10 ml anhydrous MeOH). The color of the solution changes from bright yellow to clear. Stirring was continued for 30 min. Water (50 ml) was added and the solution was extracted with Et2O (2×50 ml). The combined organic extracts were washed with brine and dried over MgSO4. Filtration and concentration in vacuo of the organic material afforded 5.44 g crude. Distillation yielded 4.38 g (83%) of 1-(3-bromopropyl)-2-phenylcyclohexanecarboxylic acid ethyl ester as a yellow viscous oil.

Workup

  1. temperaturecooled to 0°, under nitrogen
  2. waitat RT for 30 min
  3. temperatureThe flask was cooled to 0°
  4. customto destroy any excess hydride
  5. stirringStirring
  6. waitwas continued for 30 min
  7. extractionthe solution was extracted with Et2O (2×50 ml)
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationFiltration and concentration in vacuo of the organic material
  11. customafforded 5.44 g crude
  12. distillationDistillation

Sources & evidence

ORD record
ord-7353a204d3ed43a6a6dbdad18c2d2b05
Source dataset
uspto-grants-1986_06
Patent number
US04595759

Reaction notes

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