Dimethyl Sulfoxide → 1-(4-Chlorophenyl)-cyclopentanecarbaldehyde

HRID 54263

Reaction equation

HRID 54263 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([CH2:23][OH:24])[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([CH:23]=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27240171-(p-Chlorophenyl)cyclopentanemethanol

Product 1

HCID 214680001-(4-Chlorophenyl)-cyclopentanecarbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound is prepared in a manner analogous to that of Step B of Example 4, using 7.0 grams (0.055 mole) of oxalyl chloride, 9.5 grams (0.120 mole) of dimethyl sulfoxide, 10.5 grams (0.050 mole) of [1-(4-chlorophenyl)-1-cyclopentyl]methanol, and 25.5 grams (0.250 mole) of triethylamine in 175 mL of methylene chloride, yielding 1-(4-chlorophenyl)-1-cyclopentanecarboxaldehyde.

Workup

  1. customThis compound is prepared in a manner analogous to that of Step B of Example 4

Sources & evidence

ORD record
ord-77961596412b4d11bac1cca180d2c59a
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Linked notes

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