Methanol → (1-(4-Chlorophenyl)cyclobutyl)methanol

HRID 1831796Notes

Reaction equation

HRID 1831796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](O)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CO>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acid

Product 1

HCID 13083368(1-(4-Chlorophenyl)cyclobutyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 1 g 1-(4-Chloro-phenyl)-cyclobutanecarboxylic acid in 15 ml THF were added dropwise at 0° C. 9.5 ml BH3*THF in THF (1M). Then the reaction mixture was heated at reflux for 2 h and then cooled again to 0° C. followed by cautious addition of 30 ml methanol. After evaporation of the solvents the residue was codestilled twice with toluene. The crude product was subjected to the subsequent reaction without further purification.

Workup

  1. temperatureThen the reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. customAfter evaporation of the solvents the residue
  4. customThe crude product was subjected to the subsequent reaction without further purification

Sources & evidence

ORD record
ord-442f3bb3f30a447ea49e074ea1f6b996
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

Loading…