Dichloromethane → HCID 17989084, compound

HRID 1869334Notes

Reaction equation

HRID 1869334 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10](C)([CH3:20])[CH2:11][C:12]([C:16]([F:19])([F:18])[F:17])([OH:15])[CH2:13][OH:14].ClCCl.C(N(CC)CC)C.[Cl-].[NH4+]>CS(C)=O>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([CH3:20])[CH2:11][C:12]([OH:15])([C:16]([F:18])([F:19])[F:17])[CH:13]=[O:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 17989095HCID 17989095, compound

Product 1

HCID 17989084HCID 17989084, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.5 g (8.06 mmol) of rac-4-(2-fluoro-3-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol is introduced into a mixture that consists of 52 ml of dichloromethane, 14 ml of dimethyl sulfoxide and 4.08 g (40.29 mmol) of triethylamine. At room temperature, 2.57 g (16.11 mmol) of SO3/pyridine complex is added, and the batch is stirred overnight at this temperature. The reaction mixture is mixed with saturated ammonium chloride solution and stirred vigorously. After additional common working-up, 2.11 g (85%) of the desired aldehyde is obtained.

Workup

  1. additionAt room temperature, 2.57 g (16.11 mmol) of SO3/pyridine complex is added
  2. stirringstirred vigorously

Sources & evidence

ORD record
ord-b64c16e256624e60b9b892190bc2685a
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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