Water → 4-(3-Fluoropropoxy)benzaldehyde

HRID 217554

Reaction equation

HRID 217554 reaction equation
[F-:1].[K+].C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[CH:29]([C:31]1[CH:45]=[CH:44][C:34]([O:35][CH2:36][CH2:37][CH2:38]OS(C)(=O)=O)=[CH:33][CH:32]=1)=[O:30].O>C(#N)C>[F:1][CH2:38][CH2:37][CH2:36][O:35][C:34]1[CH:44]=[CH:45][C:31]([CH:29]=[O:30])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 59236855Methanesulfonic acid 3-(4-formylphenoxy)propyl ester

Product 1

HCID 27829714-(3-Fluoropropoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
60 °C

Procedure

Potassium fluoride (Fluka, 7.2 mg, 0.124 mmol) and kryptofix 222 (Fluka, 46.7 mg, 0.124 mmol) were dissolved in dry acetonitrile (2.5 ml). After 10 min the mixture was added to a stirred solution of methanesulfonic acid 3-(4-formylphenoxy)propyl ester 13 (16.0 mg, 0.062 mmol) in dry acetonitrile (1.5 ml). The reaction mixture was heated at 60° C. for 30 minutes. The product was confirmed by analytical HPLC (column Phenomenex Luna C18(2) 3 μm 4.6×50 mm, solvents: A=water/0.1% TFA and B=acetonitrile/0.1% TFA; gradient 10-80% B over 10 min; flow 2.0 ml/min, UV detection at 214 and 254 nm) co-eluting with commercial standard (Fluorochem) at 5.0 minutes.

Workup

  1. customat 5.0 minutes

Sources & evidence

ORD record
ord-6799a10eada64d6688f75700a3445624
Source dataset
uspto-grants-2012_06
Patent number
US08197793B2

Linked notes

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