Diethyl Ether → HCID 71257668, compound

HRID 2200794Notes

Reaction equation

HRID 2200794 reaction equation
[O:1]1[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]([C:22](=[O:24])[CH3:23])[CH:13]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.O1CCC[CH2:26]1.C[Mg]Br.CCOCC>>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[N:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[N:15]=[C:14]([C:22]([OH:24])([CH3:26])[CH3:23])[CH:13]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 71257714HCID 71257714, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 71257668HCID 71257668, compound

Conditions

Temperature
-78 °C

Procedure

1-[6-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl]ethanone (0.21 g, 0.60 mmol) was dissolved in tetrahydrofuran (6.00 mL, 74.0 mmol) and was cooled to −78° C., then 3.0 M methylmagnesium bromide in ether (0.30 mL, 0.90 mmol) was added. The reaction was stirred at −78° C. for 1 hour at which time LCMS analysis showed that it was mostly done. The reaction was quenched with sat. NH4Cl and was transferred to a separatory funnel and partitioned between water and EtOAc, the phases were separated and the aqueous phase was washed with additional EtOAc. The combined organic phase was washed with water, then sat. NaCl, dried over MgSO4 and filtered and the solvent removed in vacuo to leave the crude product. MS: 363 (M+H). 1H NMR (500 MHz, CDCl3): δ 6.90 (s, 1H); 5.30 (m, 1H, OCH); 3.96 (s, 4H, OCH2); 1.98 (m, 4H); 1.82 (m, 2H); 1.63 (m, 2H); 1.50 (s, 311, CH3). 13C NMR (125 MHz, CDCl3): δ 176 (s, NC); 171 (s, OC); 156 (q, N2C); 119 (q, CF3); 108 (s, O2C); 105 (s, CH); 74 (s, OCH); 73 (s, HOC); 65 (s, OCH2); 32 (s, CH2); 30 (s, CH3); 28 (s, CH2).

Workup

  1. customThe reaction was quenched with sat. NH4Cl
  2. customwas transferred to a separatory funnel
  3. custompartitioned between water and EtOAc
  4. customthe phases were separated
  5. washthe aqueous phase was washed with additional EtOAc
  6. washThe combined organic phase was washed with water
  7. dry with materialsat. NaCl, dried over MgSO4
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1218a5132c564598b59a045e8dcb7580
Source dataset
uspto-grants-2016_06
Patent number
US09359358B2

Reaction notes

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