Diethyl Ether → HCID 59593472, compound

HRID 2261242Notes

Reaction equation

HRID 2261242 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[N:4][CH:3]=1.[CH:15]1([Mg]Cl)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(OCC)C.[Cl-].[NH4+]>C1COCC1.O>[CH:9]1([C:7]([C:5]2[O:6][C:2]([CH3:1])=[CH:3][N:4]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:8])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 59593475HCID 59593475, compound2×HCID 178478990HCID 178478990, compound

Product 1

HCID 59593472HCID 59593472, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (5-methyl-oxazol-2-yl)-phenyl-methanone (intermediate 2) (3.0 g, 16 mmol) in 32 mL dry THF at 0° C. under nitrogen was treated dropwise over 10 min with a 2 M solution of cyclohexylmagnesium chloride in diethyl ether (10 mL, 20 mmol). The resulting deep yellow solution was stirred at 0° C. for about 30 min during which time a precipitate was formed, and then at RT for 1.5 h. The reaction mixture was cooled to 0° C. again and treated cautiously with satd. ammonium chloride solution (aq.). The mixture was stirred at RT for 10 min then diluted with water (10 mL). The phases were separated and the organic phase was washed with brine. The combined aqueous phase was extracted with DCM and the combined organic phase was dried (MgSO4) and concentrated in vacuo to give the crude product, which was triturated with ether, filtered off and dried.

Workup

  1. customwas formed
  2. waitat RT for 1.5 h
  3. temperatureThe reaction mixture was cooled to 0° C. again
  4. additiontreated cautiously with satd
  5. stirringThe mixture was stirred at RT for 10 min
  6. customThe phases were separated
  7. washthe organic phase was washed with brine
  8. extractionThe combined aqueous phase was extracted with DCM
  9. dry with materialthe combined organic phase was dried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ae660c5558b4908bb3914e8b0efd3f6
Source dataset
uspto-grants-2010_12
Patent number
US07846955B2

Reaction notes

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