Diethyl Ether → HCID 71257658, compound

HRID 2200792Notes

Reaction equation

HRID 2200792 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]([CH:22]=[O:23])[CH:13]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:24][Mg]Br.CCOCC>O1CCCC1>[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]([CH:22]([OH:23])[CH3:24])[CH:13]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 86676920HCID 86676920, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 71257658HCID 71257658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

6-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidine-4-carbaldehyde (described in Example 1, Step 3) (0.20 g, 0.60 mmol) was dissolved in tetrahydrofuran (6.00 mL) 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 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 then the solvent removed in vacuo to leave the crude product. The crude material used in the next reaction without purification. MS: 371 (M+Na+), 349 (M+1).

Workup

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

Sources & evidence

ORD record
ord-f565f14450724811819d443c0289efb1
Source dataset
uspto-grants-2016_06
Patent number
US09359358B2

Reaction notes

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