Tetrahydrofuran → HCID 178472398, compound

HRID 2095652Notes

Reaction equation

HRID 2095652 reaction equation
I[C:2]1[C:3]([CH3:19])=[N:4][N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:6]=1[CH3:7].C1COCC1.C([Mg]Cl)(C)C.CO[B:32]1[O:36][C:35]([CH3:38])([CH3:37])[C:34]([CH3:40])([CH3:39])[O:33]1>>[CH3:19][C:3]1[C:2]([B:32]2[O:36][C:35]([CH3:38])([CH3:37])[C:34]([CH3:40])([CH3:39])[O:33]2)=[C:6]([CH3:7])[N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)[N:4]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418918HCID 178418918, compoundHCID 178472402HCID 178472402, compound

Product 1

HCID 178472398HCID 178472398, compound

Procedure

To a solution of ethyl trans-4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)cyclohexane-carboxylate (100.0 mg, 0.2658 mmol) in THF (5 mL, 60 mmol) was added 2 M isopropylmagnesium chloride in THF (0.5316 mL, 1.063 mmol) at rt, and the mixture was stirred for 30 min. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.2178 mL, 1.329 mmol) was added, and the mixture stirred at rt overnight. The reaction was quenched with sat. NH4Cl, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was concentrated in vacuo to afford the title compound as a clear oil.

Workup

  1. stirringthe mixture stirred at rt overnight
  2. customThe reaction was quenched with sat. NH4Cl
  3. customthe organic solvent was removed in vacuo
  4. extractionThe material was extracted with DCM and water
  5. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-8a3666b9f1274787973cdc38e2578422
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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