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

HRID 967461Notes

Reaction equation

HRID 967461 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-09aa32fe2f9d46c5ae483d9d94d0e8c6
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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