Acetone → 4-{[6-(2-Hydroxyethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexanone

HRID 2200801Notes

Reaction equation

HRID 2200801 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:15]=[C:14]([CH2:22][CH2:23][OH:24])[CH:13]=3)[CH2:7][CH2:6]2)[O:4]CC1.CC(C)=O.Cl.O.C(=O)(O)[O-]>>[OH:24][CH2:23][CH2:22][C:14]1[N:15]=[C:16]([C:18]([F:19])([F:20])[F:21])[N:17]=[C:12]([O:11][CH:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[CH:13]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 962WaterHCID 712573092-[6-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl]ethanol

Product 1

HCID 712575084-{[6-(2-Hydroxyethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}cyclohexanone

Procedure

2-[6-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl]ethanol was dissolved in acetone (60 mL, 900 mmol), and 5.0 M hydrogen chloride in water (20 mL, 98 mmol) was added and stirred for 17 hours. LCMS and HPLC analysis showed nearly complete conversion to M+H 305. Aqueous bicarbonate was added and the reaction mixture was stirred, then concentrated. This mixture was extracted with EtOAc. The EtOAc was dried (Na2SO4), and evaporated in vacuo to give 1.3 g light yellow viscous oil (used in the next reaction without purification). 1H NMR (300 MHz, CDCl3): δ6.80 (s, 1H); 5.60 (m, 1H, OCH); 4.06 (t, 2H, OCH2); 3.04 (t, 2H, CH2); 2.61 (m, 2H); 2.45 (m, 2H); 2.25 (m, 2H).

Workup

  1. stirringthe reaction mixture was stirred
  2. concentrationconcentrated
  3. extractionThis mixture was extracted with EtOAc
  4. dry with materialThe EtOAc was dried (Na2SO4)
  5. customevaporated in vacuo
  6. customto give 1.3 g light yellow viscous oil (
  7. customused in the next reaction without purification)

Sources & evidence

ORD record
ord-5e8d67d770c94ca4a9722a777a1af6b5
Source dataset
uspto-grants-2016_06
Patent number
US09359358B2

Reaction notes

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