Water → 4-{[4-(1-Hydroxy-1-methylethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy}cyclohexanone

HRID 2200820Notes

Reaction equation

O1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[C:16]([C:18]([OH:21])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[N:13]=3)[CH2:7][CH2:6]2)[O:4]CC1.O>CC(C)=O.Cl>[OH:21][C:18]([C:16]1[CH:15]=[C:14]([C:22]([F:24])([F:25])[F:23])[N:13]=[C:12]([O:11][CH:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[CH:17]=1)([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

2-[2-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-6-(trifluoromethyl)pyridin-4-yl]propan-2-ol (0.049 g, 0.14 mmol) was dissolved in acetone (3.7 mL) A solution of 12.0 M hydrogen chloride in water (0.43 mL, 5.2 mmol) was added and was stirred at 25° C. for 16 hours at which time LCMS showed about 70% reaction was complete. An additional 12.0 M hydrogen chloride in water (0.43 mL, 5.2 mmol) was added and was stirred for 3 hours; LCMS showed ˜90% reaction was complete and was quenched into excess NaHCO3, extracted with EtOAc and the organic extract was evaporated to give the product. This was used in the next reaction without purification. MS (ES): 318 (M+1).

Workup

additionwas added
customabout 70% reaction
stirringwas stirred for 3 hours
custom˜90% reaction
customwas quenched into excess NaHCO3
extractionextracted with EtOAc
extractionthe organic extract
customwas evaporated
customto give the product
customThis was used in the next reaction without purification

Sources & evidence

ORD record: ord-d4bdafcefe87461fbc0464dafd7e641b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359358B2

Reaction notes

Loading…