Sodium hydride → 2-[2-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-6-(trifluoromethyl)pyridin-4-yl]propan-2-ol

HRID 2200819Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl[C:13]1[CH:18]=[C:17]([C:19]([OH:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[N:14]=1.[H-].[Na+]>O1CCCC1>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:13]3[CH:18]=[C:17]([C:19]([OH:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([F:24])([F:26])[F:25])[N:14]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

1,4-Dioxaspiro[4.5]decan-8-ol (0.25 g, 1.58 mmol) and 2-[2-chloro-6-(trifluoromethyl)pyridin-4-yl]propan-2-ol (0.2 g, 0.835 mmol) were dissolved in tetrahydrofuran (2 mL) and cooled to 0° C. and a 60% mixture of sodium hydride (70.0 mg, 1.75 mmol) in mineral oil was added and the reaction was stirred for 30 minutes at 0° C. and at 25° C. for 60 hours at which time TLC analysis indicated the presence of some product. The reaction was quenched with water, and was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4), and evaporated in vacuo. The residue was purified by LC (pH 2) to give the product. MS (ES): 362 (M+1).

Workup

customThe reaction was quenched with water
extractionwas extracted with ethyl acetate
washthe organic extracts were washed with water, saturated NaCl
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe residue was purified by LC (pH 2)
customto give the product

Sources & evidence

ORD record: ord-6f5352fe224145fe868317cafd1af62d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359358B2

Reaction notes

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