Hydrochloric Acid → HCID 63215470, compound

HRID 1437611Notes

Reaction equation

HRID 1437611 reaction equation
C1CCN2C(=NCCC2)CC1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]#[N:22].[CH2:25]=[O:26].Cl>C1COCC1.O>[F:12][C:13]([F:23])([F:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([CH2:25][OH:26])[C:21]#[N:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 764352-(Trifluoromethyl)phenylacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 63215470HCID 63215470, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 50 μL (0.33 mmol) sample of DBU was injected into a stirred solution of 2-(2-(trifluoromethyl)phenyl)ethanenitrile (0.995 g, 4.86 mmol) and formaldehyde (600 μL of 30%) in THF (3 mL), producing a mild exotherm. After 45 min, the mixture was acidified (3N HCl), diluted with water and extracted with ethyl acetate. The organic phase was water washed, dried (MgSO4) and stripped. The resulting colorless oil was flash chromatographed on silica gel (22 g) eluting with CH2Cl2 →40% ethyl acetate/CH2Cl2. Fractions containing only product (Rf 0.5 (silica gel, EtOAc:hexane=1:4)) were stripped to give 1.08 g (94% yield) of the desired alcohol.

Workup

  1. customproducing a mild exotherm
  2. extractionextracted with ethyl acetate
  3. washwashed
  4. dry with materialdried (MgSO4)
  5. customchromatographed on silica gel (22 g)
  6. washeluting with CH2Cl2 →40% ethyl acetate/CH2Cl2
  7. additionFractions containing only product (Rf 0.5 (silica gel, EtOAc:hexane=1:4))

Sources & evidence

ORD record
ord-808da97f5af7419ca14d8191bc1fa33a
Source dataset
uspto-grants-2009_11
Patent number
US07622504B2

Reaction notes

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