Triethylamine → 4-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

HRID 2182655Notes

Reaction equation

HRID 2182655 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([C:14]([F:17])([F:16])[F:15])([OH:13])[CH2:11][OH:12])[CH:7]=1.C(N(CC)CC)C.[NH4+].[Cl-]>CS(C)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:13])([C:14]([F:17])([F:16])[F:15])[CH:11]=[O:12])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 219489282-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanol

Product 1

HCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 g (4.8 mmol) of 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol and 3.4 ml (24.4 mmol) of triethylamine in 17 ml of DMSO and 53 ml of CH2Cl2 are mixed at 10° C. in portions with 3 g (18.9 mmol) of pyridine-sulfur trioxide complex. After 3 hours at 12-18° C., it is hydrolyzed while being cooled with ice with saturated NH4Cl solution, and it is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated by evaporation: 1.57 g of the product as a light yellow oil.

Workup

  1. extractionis extracted with ethyl acetate
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9dc248a587f74cc195f2a283820e7c48
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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